Water → 1-(2,3-dimethoxy-6,7-dihydro-5H-benzo-cyclohepten-8-ylcarbonyl)-2-methoxymethyl-4-(3,4,5-tri-methoxybenzyl)piperazine

HRID 358778Notes

Reaction equation

HRID 358778 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.[CH3:19][O:20][CH2:21][CH:22]1[NH:27][CH2:26][CH2:25][N:24]([CH2:28][C:29]2[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=2)[CH2:23]1.C(N(CC)CC)C.O>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:27]3[CH2:26][CH2:25][N:24]([CH2:28][C:29]4[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=4)[CH2:23][CH:22]3[CH2:21][O:20][CH3:19])=[O:14])=[CH:8][C:7]=2[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10264946HCID 10264946, compoundHCID 200665833-Methoxymethyl-1-(3,4,5trimethoxybenzyl)piperazine

Product 1

HCID 103925171-(2,3-dimethoxy-6,7-dihydro-5H-benzo-cyclohepten-8-ylcarbonyl)-2-methoxymethyl-4-(3,4,5-tri-methoxybenzyl)piperazineYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonyl chloride (0.36 g) in dichloromethane (6 ml) is added dropwise, at 0° C. while stirring, to a mixture of 3-methoxymethyl-1-(3,4,5trimethoxybenzyl)piperazine (0.4 g) obtained in Reference Example 14, triethylamine (0.3 g) and dichloromethane (6 ml). After stirring at room temperature for one hour, the reaction mixture is added to 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 afford 1-(2,3-dimethoxy-6,7-dihydro-5H-benzo-cyclohepten-8-ylcarbonyl) -2-methoxymethyl-4-(3,4,5-tri-methoxybenzyl)piperazine (0.6 g) as a colorless oily product. This product is converted to the hydrochloride, and treated with ethyl ether to give pale yellow powder.

Workup

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

Sources & evidence

ORD record
ord-b4560870b9e5436190d2a881e4986444
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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