Diisopropylethylamine → 2-[4-Phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]piperidine-1-carboxylic acid tert-butyl ester

HRID 720910Notes

Reaction equation

HRID 720910 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[C:18]1([CH2:24][CH2:25][CH2:26][CH:27]([NH2:37])[CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:16])[NH:37][CH:27]([CH2:26][CH2:25][CH2:24][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 2724699PyBOPHCID 218922551,7-Diphenyl-4-aminoheptane hydrochloride

Product 1

HCID 121367652-[4-Phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butoxycarbonyl-piperidine-2-carboxylic acid (3 g; 13.1 mmol) is dissolved in methylene chloride (100 mL) at ambient temperature. 1,7-Diphenyl-4-aminoheptane hydrochloride (1) (4.77 g; 15.7 mmol), diisopropylethylamine (7.3 mL; 41.9 mmol), and PyBOP (8.17 g; 15.7 mmol) are added sequentially. The mixture is stirred for 17 hours at ambient temperature then concentrated in vacuo at 40° C. The residue is purified via silica gel chromatography with gradient elution (10%→30% ethyl acetate in hexanes) affording the desired product as an oil. ESMS:MH+ 479.4

Workup

  1. concentrationthen concentrated in vacuo at 40° C
  2. customThe residue is purified via silica gel chromatography with gradient elution (10%→30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-26703f6d53d94a44970d6afe8837da2c
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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