Benzyl piperazine-1-carboxylate → HCID 67386829, compound

HRID 2408846Notes

Reaction equation

HRID 2408846 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15](O)=[O:16])[C:9]2=[O:18])=[CH:4][CH:3]=1.[N:26]1([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]([N:29]3[CH2:30][CH2:31][N:26]([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])[CH2:27][CH2:28]3)=[O:16])[C:9]2=[O:18])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 643495Benzyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673591112-(3,3-Bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetic acid

Product 1

HCID 67386829HCID 67386829, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3,3-bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetic acid (0.34 g, 1.0 mmol, Example 23D) 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 to the reaction, and the 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 afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.39-7.31 (m, 5H), 7.30-7.21 (m, 4H), 6.97 (dd, J=9.7, 7.7, 4H), 5.15 (s, 2H), 4.19 (s, 2H), 3.70-3.59 (m, 2H), 3.58-3.37 (m, 8H), 2.64-2.52 (m, 2H), 1.90-1.76 (m, 2H); MS (DCI +) m/z 565 (M+MH4)+.

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-42f9241da008443bb6a4ed97fcb70fda
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

Loading…