1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69216966, compound

HRID 279310

Reaction equation

HRID 279310 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([NH:24][C@@H:25]([C:33](O)=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23])([CH3:20])([CH3:19])[CH3:18].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)(Cl)Cl.CCN(CC)CC>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:33](=[O:34])[C@@H:25]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[NH:24][C:22]([O:21][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:23])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 637610Boc-D-phenylalanineHCID 18426145{[1-(4-Chlorobenzyl)piperidin-4-yl]methyl}amine

Product 1

HCID 69216966HCID 69216966, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 1-(4-chlorobenzyl)-4-(aminomethyl)piperidine (100 mg) in CHCl3 (3 mL) was treated with Et3N (0.090 mL), N-(tert-butoxycarbonyl)-D-phenylalanine (122 mg), EDCI (89 mg) and HOBt (62 mg). The reaction mixture was stirred at room temperature for 17 h. The reaction mixture was washed with 1 N aqueous NaOH solution (2 mL×2) and brine (2 mL). The organic layer was dried and concentrated to afford 1-(4-chlorobenzyl)-4-[{N-(tert-butoxycarbonyl)-D-phenylalanyl}aminomethyl]piperidine.

Workup

  1. washThe reaction mixture was washed with 1 N aqueous NaOH solution (2 mL×2) and brine (2 mL)
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-271d712915234380ac470461f9fbd88a
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Linked notes

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