Water → Methyl 4-benzyloxycarbonyl-1-(3,4,5-trimethoxybenzoyl)-piperazine-2-carboxylate

HRID 358773Notes

Reaction equation

HRID 358773 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([O:41][CH3:42])[C:38]=1[O:39][CH3:40])[C:33](Cl)=[O:34].O>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:33](=[O:34])[C:32]2[CH:31]=[C:30]([O:29][CH3:28])[C:38]([O:39][CH3:40])=[C:37]([O:41][CH3:42])[CH:36]=2)[CH:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 27573841-Benzyl 3-methyl piperazine-1,3-dicarboxylate

Product 1

HCID 54552702Methyl 4-benzyloxycarbonyl-1-(3,4,5-trimethoxybenzoyl)-piperazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of methyl 4-benzyloxycarbonylpiperazine-2-carboxylate (1.2 g) obtained in Reference Example 21, triethylamine (0.9 g) and dichloromethane (15 ml) is added dropwise, taking 5 minutes while stirring at 0° C., to a solution of 3,4,5-trimethoxybenzoyl chloride (1.08 g) in dichloromethane (10 ml). The reaction mixture is stirred at room temperature for 10 minutes, and then poured into water, followed by extraction with dichloromethane. The organic layer is washed with water and dried, then the solvent is distilled off under reduced pressure. The residue is purified by means of a silica gel column chromatography (hexane:ethyl acetate:acetone=2:2:1) to give methyl 4-benzyloxycarbonyl-1-(3,4,5-trimethoxybenzoyl)-piperazine-2-carboxylate as a colorless oily product (2.1 g).

Workup

  1. additionis added dropwise
  2. extractionfollowed by extraction with dichloromethane
  3. washThe organic layer is washed with water
  4. customdried
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by means of a silica gel column chromatography (hexane:ethyl acetate:acetone=2:2:1)

Sources & evidence

ORD record
ord-a94ee1676c654839b73020d5920a7f4b
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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