Triethylamine → ethyl 4-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine-2-carboxylate

HRID 358774Notes

Reaction equation

HRID 358774 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13](Cl)=[O:14])=[CH:8][C:7]=2[CH:16]=1.Cl.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH:21]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:23]3[CH2:24][CH2:25][NH:20][CH:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22]3)=[O:14])=[CH:8][C:7]=2[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10264946HCID 10264946, compoundHCID 20066599Ethyl piperazine-2-carboxylate hydrochloride

Product 1

HCID 10249683ethyl 4-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine-2-carboxylateYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonylchloride (1.1 g) in dichloromethane (12 ml) is added dropwise, taking 30 minutes while stirring under ice-cooling, to a mixture of ethyl piperazine-2-carboxylate hydrochloride (1.0 g), triethylamine (0.5 g) and dichloromethane (20 ml). The reaction mixture is stirred for one hour at 0 ° C, and then poured into ice-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=1:1:1) to afford ethyl 4-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine-2-carboxylate as crystals (1.2 g). This product is recrystallized form ethyl acetate and hexane to give colorless prisms, m.p. 105-106° C.

Workup

  1. stirringThe reaction mixture is stirred for one hour at 0 ° C
  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=1:1:1)

Sources & evidence

ORD record
ord-118d593301e64a48a06d76945cd1dde4
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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