Benzyl piperazine-1-carboxylate → HCID 67387134, compound

HRID 2408848Notes

Reaction equation

HRID 2408848 reaction equation
[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20](O)=[O:21].[N:23]1([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:1]=[C:2]1[C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([N:26]1[CH2:27][CH2:28][N:23]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:24][CH2:25]1)=[O:21]

Participants

6

Reactant 3

HCID 643495Benzyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 67387134HCID 67387134, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (0.29 g, 1.0 mmol, Example 21C) in CH2Cl2 (15 mL) was added benzyl piperazine-1-carboxylate (0.22 g, 1.0 mmol) under nitrogen. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.38 g, 2.0 mmol) and 4-(dimethylamino)pyridine (0.012 g, 0.1 mmol) were added, and the reaction mixture was stirred overnight at room temperature. The organic layer was washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; CH3OH/CH2Cl2, 2:98 eluant) to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.43-7.16 (m, 15H), 5.14 (s, 2H), 4.19 (s, 2H), 3.64-3.23 (m, 10H), 2.81 (t, J=6.5, 2H); MS (DCI+) m/z 414 (M+H)+.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; CH3OH/CH2Cl2, 2:98 eluant)

Sources & evidence

ORD record
ord-a9066b9a88914e34afc274434ab0eac5
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

Loading…