Acetic Anhydride → HCID 10030881, compound

HRID 358783Notes

Reaction equation

HRID 358783 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:37][CH3:38])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH2:17][CH:16]3[CH2:34][OH:35])=[O:14])=[CH:8][C:7]=2[CH:36]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:39]([O:35][CH2:34][CH:16]1[CH2:17][N:18]([CH2:21][C:22]2[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=2)[CH2:19][CH2:20][N:15]1[C:13]([C:9]1[CH2:10][CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([O:37][CH3:38])[C:3]([O:2][CH3:1])=[CH:36][C:7]=2[CH:8]=1)=[O:14])(=[O:41])[CH3:40]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10436901HCID 10436901, compound

Product 1

HCID 10030881HCID 10030881, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -4-(3,4,5-trimethoxybenzyl)piperazine-2-methanol (500 mg), acetic anhydride (153 mg), triethylamine (150 mg), 4dimethylaminopyridine (10 mg) and methylene chloride (5 ml) is stirred for 20 hours at room temperature. To the reaction mixture is added methylene chloride, and the organic layer is washed with an aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent:ethyl acetate) to give 2-acetoxymethyl-1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -4-(3,4,5-trimethoxybenzyl)piperazine (420 mg). This product is converted to its hydrochloride, followed by recrystallization from ethanol to give colorless prisms, m.p. 135-139° C.

Workup

  1. washthe organic layer is washed with an aqueous solution of sodium hydrogencarbonate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate is purified by means of a silica gel column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-af2ea60860234b2fb4460ab7b7868dea
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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