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640042

Sigma-Aldrich

4-Amino-1-Boc-piperidine

97%

Synonym(s):

1-Boc-4-piperidinamine, tert-Butyl 4-amino-1-piperidinecarboxylate

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About This Item

Empirical Formula (Hill Notation):
C10H20N2O2
CAS Number:
87120-72-7
Molecular Weight:
200.28
MDL number:
MFCD01076201
UNSPSC Code:
12352100
PubChem Substance ID:
24883073
NACRES:
NA.22

Assay

97%

form

solid

SMILES string

CC(C)(C)OC(=O)N1CCC(N)CC1

InChI

1S/C10H20N2O2/c1-10(2,3)14-9(13)12-6-4-8(11)5-7-12/h8H,4-7,11H2,1-3H3

InChI key

LZRDHSFPLUWYAX-UHFFFAOYSA-N

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Application

4-Amino-1-Boc-piperidine can be used:
  • as a starting material in the synthesis of N-(3-(4-hydroxyphenyl)-propenoyl)-amino acid tryptamides, which can act as silent information regulator human type 2 (SIRT2) inhibitors
  • to synthesize piperidine-substituted triazine derivativesand piperidinylamino-diarylpyrimidine (pDAPY) derivatives as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (HIV-1 NNRTIs)
Employed in a microwave-assisted solid-phase synthesis of N-substituted piperidines via direct annulation of primary amines with resin-bound dimesylates.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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"Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors"
Chen X, et al.
European Journal of Organic Chemistry, 51, 60-66 (2012)
"Novel piperidinylamino-diarylpyrimidine derivatives with dual structural conformations as potent HIV-1 non-nucleoside reverse transcriptase inhibitors"
Chen X, et al.
Bioorganic & Medicinal Chemistry, 23(24), 6593-6597 (2013)
"N-(3-(4-Hydroxyphenyl)-propenoyl)-amino acid tryptamides as SIRT2 inhibitors"
Kiviranta.HP, et al.
Bioorganic & Medicinal Chemistry, 17(09), 2448-2451 (2007)
Calum Macleod et al.
Journal of combinatorial chemistry, 8(1), 132-140 (2006-01-10)
The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates. Critical to the success of this chemistry was the development of alpha-methyl benzyl carbamate resin linker.

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