2-Chlorobenzylamine → 1-Tert-butyl 4-methyl 4-(2-chlorobenzylcarbamoyl)piperidine-1,4-dicarboxylate

Participants

Role	Name	HCID	Charge
Reactant	2-Chlorobenzylamine	HCID 66648	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	1-((Tert-butoxy)carbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid	HCID 57920282	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-Tert-butyl 4-methyl 4-(2-chlorobenzylcarbamoyl)piperidine-1,4-dicarboxylate	HCID 59778564	52%

Reaction Steps

To a solution of 1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid (3.7 g, 13.2 mmol) in DMF (30 mL) were added HATU (6.0 g, 15.8 mmol, 1.2 equiv.), 2-chlorobenzylamine (1.9 mL, 15.8 mmol, 1.2 equiv.) and DIEA (228 μL, 1.31 mmol, 0.1 equiv.). The reaction mixture was stirred for 3 h and purified on RP-HPLC using a mixture of acetonitrile and H2O to give 1-tert-butyl 4-methyl 4-(2-chlorobenzylcarbamoyl)piperidine-1,4-dicarboxylate (2.8 g, 52%). LRMS (M+H+-Boc) m/z 311.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08071625B2
Source dataset	uspto-grants-2011_12
ORD ID	ord-78c19bf64edd47b49fcd48e7e999c63d
Source note	uspto-grants-2011_12