Trifluoroacetic acid → Methyl-phenyl-carbamic Acid 4-{2-[(1-methyl-piperidine-4-carbonyl)-amino]-ethyl}-phenyl Ester

HRID 1180041

Reaction equation

HRID 1180041 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[NH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39](=[O:48])[N:40]([CH3:47])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:34][CH:33]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:8]([NH:29][CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][C:39](=[O:48])[N:40]([CH3:47])[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:36][CH:37]=2)=[O:10])[CH2:6][CH2:7]1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27369391-Methylpiperidine-4-carboxylic acidHCID 69520583Methyl-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl Ester

Product 1

HCID 69520479Methyl-phenyl-carbamic Acid 4-{2-[(1-methyl-piperidine-4-carbonyl)-amino]-ethyl}-phenyl EsterYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-methylpiperidine-4-carboxylic acid (0.3 mmol), EDAC (0.36 mmol) and triethylamine (1.0 mmol) in CH2Cl2 (10 mL) was added N-hydroxybenzoetriazole and N-methyl-N-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl ester as its TFA salt (0.3 mmol). The mixture was stirred 16 h at rt and purified by preparative HPLC (Gilson) to give the title compound in 5% yield as an oil.

Workup

  1. custompurified by preparative HPLC (Gilson)

Sources & evidence

ORD record
ord-e1941e576dcc474dbfc7b2b914d0e013
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Linked notes

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