Chloroacetyl chloride → 1,1-Dimethylethyl 4-(chloroacetyl)-3-[hydroxy(diphenyl)methyl]piperazine-1-carboxylate

HRID 1713505Notes

Reaction equation

HRID 1713505 reaction equation
[OH:1][C:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:3]1[NH:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.C(N(C(C)C)CC)(C)C.[Cl:37][CH2:38][C:39](Cl)=[O:40].C(OCC)(=O)C>O1CCCC1>[Cl:37][CH2:38][C:39]([N:8]1[CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH:3]1[C:2]([OH:1])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:40]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 23122074(1,1-Dimethylethyl)3-(hydroxydiphenylmethyl)-1-piperazine carboxylate

Product 1

HCID 684196211,1-Dimethylethyl 4-(chloroacetyl)-3-[hydroxy(diphenyl)methyl]piperazine-1-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-[hydroxy(diphenyl)methyl]-1-piperazine carboxylate (0.50 g, 1.4 mmol) in tetrahydrofuran (5 mL) were sequentially added diisopropylethylamine (2 mL) and chloroacetyl chloride (0.46 g, 4.1 mmol) with ice cooling, and the mixture was stirred for 4 hours while elevating the temperature to room temperature. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (0.28 g, yield 46%).

Workup

  1. customto room temperature
  2. washthe resulting mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c38e1ae7b0d04d508f5b9bdb775befe9
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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