Chloroform → 1-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine

HRID 133596

Reaction equation

HRID 133596 reaction equation
ClCCl.[F:4][C:5]([F:20])([F:19])[C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:9](Cl)=[O:10].[Cl:21][C:22]1[CH:40]=[CH:39][C:25]([CH2:26][N:27]2[CH2:32][CH2:31][CH:30]([CH2:33][NH:34][C:35](=[O:38])[CH2:36][NH2:37])[CH2:29][CH2:28]2)=[CH:24][CH:23]=1.C(Cl)(Cl)Cl>CO>[Cl:21][C:22]1[CH:40]=[CH:39][C:25]([CH2:26][N:27]2[CH2:28][CH2:29][CH:30]([CH2:33][NH:34][C:35](=[O:38])[CH2:36][NH:37][C:9](=[O:10])[C:8]3[CH:7]=[C:6]([C:5]([F:20])([F:19])[F:4])[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=3)[CH2:31][CH2:32]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6344Dichloromethane2×HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 184261551-(4-Chlorobenzyl)-4-((glycylamino)methyl}piperidine

Product 1

HCID 184262011-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A dichloromethane (1 mL) solution of 3,5-bis(trifluoromethyl)benzoyl chloride (0.058 mmol) was added to a mixture of 1-(4-chlorobenzyl)-4-[(glycylamino)methyl]piperidine (0.050 mmol) with chloroform (0.2 mL), a piperidinomethylpolystyrene (58 mg) and dichloromethane (0.75 mL). The resulting reaction mixture was stirred at room temperature for 2 hours, and methanol (1.0 mL) was then added to the obtained mixture. The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was loaded onto a Varian™ SCX column and washed with methanol (16 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 (6 mL) and concentrated to thereby provide 1-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No. 1213) (24.0 mg, 90%). The purity was determined by RPLC/MS (100%). ESI/MS m/e 536.2 (M++H, C24H24ClF6N3O2).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  3. washwashed with methanol (16 mL)
  4. customThe obtained crude product
  5. washwas eluted with a 2 M methanol solution of NH3 (6 mL)
  6. concentrationconcentrated to thereby provide 1-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No

Sources & evidence

ORD record
ord-8a61569f96114cb8bb403549dc6d81ad
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Linked notes

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