Triethylamine → HCID 86617473, compound

HRID 1162816Notes

Reaction equation

HRID 1162816 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH2:11][NH:10][CH2:9][CH:8]2[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][CH:3]=1.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH2:11][N:10]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:9][CH:8]2[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 86074989HCID 86074989, compound

Product 1

HCID 86617473HCID 86617473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl [1-(4-fluorobenzyl)-6-oxo-piperazin-2-yl]acetate (3.7 g, 12.5 mmol) in dichloromethane (100 mL) was added benzyl chloroformate (2.2 mL, 15.1 mmol) and triethylamine (3.5 mL, 25.1 mmol), stirred over night. The reaction mixture was diluted with dichloromethane, washed with 1N HCl, water and brine, dried over sodium sulfate, filtered and concentrated to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.23-7.38 (m, 7H), 7.01 (t, J=8.6 Hz, 2H), 5.12-5.22 (m, 3H), 4.40-4.56 (m, 1H), 3.90-4.24 (m, 5H), 3.72-3.86 (m, 1H), 3.04-3.18 (m, 1H), 2.49-2.62 (m, 2H), 1.12-1.28 (m, 3H). ES MS (M+1)=429.24.

Workup

  1. washwashed with 1N HCl, water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-21774f11b4ec45d793fc434ac2b09c34
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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