Hydrochloric Acid → 1-(7,8-Dimethoxy2,3-dihydro-1-benzoxepin-4-ylcarbonyl)-2-methoxymethyl4-(3,4,5-trimethoxybenzoyl)piperazine

HRID 358777Notes

Reaction equation

HRID 358777 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[O: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]([C:28](=[O:41])[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.Cl.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[O:12][CH2:11][CH2:10][C:9]([C:13]([N:27]3[CH2:26][CH2:25][N:24]([C:28](=[O:41])[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 313Hydrochloric AcidHCID 8471TriethylamineHCID 104682747,8-Dimethoxy-2,3-dihydro-1-benzoxepine-4-carbonyl chlorideHCID 200665933-Methoxymethyl-1-(3,4,5-trimethoxybenzoyl)piperazine

Product 1

HCID 216252111-(7,8-Dimethoxy2,3-dihydro-1-benzoxepin-4-ylcarbonyl)-2-methoxymethyl4-(3,4,5-trimethoxybenzoyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7,8-dimethoxy-2,3-dihydro-1-benzoxepine-4-carbonyl chloride (300 mg) in dichloromethane (10 ml) is added dropwise, taking 30 minutes under ice-cooling while stirring, to a mixture of 3-methoxymethyl-1-(3,4,5-trimethoxybenzoyl)piperazine×hydrochloride (400 mg) obtained in Reference Example 6, triethylamine (1 ml) and dichloromethane (30 ml). The reaction mixture is washed with an aqueous solution of citric acid and an aqueous solution of sodium hydrogencarbonate, then dried over magnesium sulfate, followed by concentration. The concentrate is subjected to a silica gel column chromatography (eluent: ethyl acetate-methanol =95:5) to afford 1-(7,8-dimethoxy2,3-dihydro-1-benzoxepin-4-ylcarbonyl) -2-methoxymethyl4-(3,4,5-trimethoxybenzoyl)piperazine (520 mg) as colorless crystals, m.p. 142° C.

Workup

  1. temperaturecooling
  2. washThe reaction mixture is washed with an aqueous solution of citric acid
  3. dry with materialan aqueous solution of sodium hydrogencarbonate, then dried over magnesium sulfate
  4. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-d1776094d76841359daecf25d73335d5
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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