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

HRID 358769Notes

Reaction equation

HRID 358769 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][CH3:29])=[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][CH3:29])=[O:27])[CH2:22]3)=[O:14])=[CH:8][C:7]=2[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10264946HCID 10264946, compoundHCID 20066636Methyl piperazine-2-carboxylate hydrochloride

Product 1

HCID 20066640methyl 4-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine-2carboxylateYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonyl chloride (2.14 g) in dichloromethane (20 ml) is added dropwise, taking 40 minutes while stirring at 0° C., to a mixture of methyl piperazine-2-carboxylate hydrochloride (1.75 g), triethylamine (3.2 g) and dichloromethane (40 ml). The reaction mixture is poured into ice-water and shaken. The organic layer is separated and subjected to distillation under reduced pressure. The residue is dissolved in 1N-HCl (20 ml) and washed with ethyl acetate. The aqueous layer is separated and then neutralized with sodium hydrogencarbonate, followed by extraction with dichloromethane. The organic layer is dried, and the solvent is distilled off. Crystals obtained from the residue are recrystallized from ethyl acetate - hexane to afford methyl 4-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine-2carboxylate as colorless needles (2.45 g), m.p. 103-104° C.

Workup

  1. customThe organic layer is separated
  2. distillationsubjected to distillation under reduced pressure
  3. dissolutionThe residue is dissolved in 1N-HCl (20 ml)
  4. washwashed with ethyl acetate
  5. customThe aqueous layer is separated
  6. extractionfollowed by extraction with dichloromethane
  7. customThe organic layer is dried
  8. distillationthe solvent is distilled off
  9. customCrystals obtained from the residue
  10. customare recrystallized from ethyl acetate - hexane

Sources & evidence

ORD record
ord-105a645ea07b4fbebb688f4b5af2f9f8
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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