Tetrahydrofuran → HCID 12669332, compound

HRID 223243Notes

Reaction equation

HRID 223243 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:31][CH3:32])=[CH:5][C:6]2[CH:12]([CH2:13][O:14][CH2:15][CH2:16]OS(C3C=CC([N+]([O-])=O)=CC=3)(=O)=O)[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:30]=1.CO[CH:35]1[CH2:40][NH:39][CH2:38][CH2:37][N:36]1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(N(CC)CC)C.[O:54]1CCC[CH2:55]1>>[CH3:1][O:2][C:3]1[C:4]([O:31][CH3:32])=[CH:5][C:6]2[CH:12]([CH2:13][O:14][CH2:15][CH2:16][N:39]3[CH2:40][CH2:35][N:36]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][C:46]=4[O:54][CH3:55])[CH2:37][CH2:38]3)[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:30]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12669330HCID 12669330, compoundHCID 20200458HCID 20200458, compound

Product 1

HCID 12669332HCID 12669332, compoundYield 82%

Procedure

A mixture of 0.50 g (1.07 mmoles) of [2-[(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)methoxy]ethyl]-4-nitrobenzenesulfonate, 0.22 g (1.07 mmoles) of o-methoxyphenylpiperazine, 0.15 ml (1.07 mmoles) of triethylamine, and 20 ml of tetrahydrofuran is stirred at room temperature for 24 hours. After removing the tetrahydrofuran in vacuo, the reaction mixture is extracted with methylene chloride and aqueous sodium bicarbonate. The organic layer is filtered through sodium sulfate, taken to dryness, and chromatographed on silica gel using 3% methanol methylene chloride eluent to give 0.40 g (82%) of 1-[2-[(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)methoxy]ethyl]-4-(2-methoxyphenyl)piperazine. The dihydrochloride salt was prepared with hydrochloric acid in ethyl ether, m.p. 172°-175°.

Workup

  1. customAfter removing the tetrahydrofuran in vacuo
  2. extractionthe reaction mixture is extracted with methylene chloride and aqueous sodium bicarbonate
  3. filtrationThe organic layer is filtered through sodium sulfate
  4. customchromatographed on silica gel using 3% methanol methylene chloride eluent

Sources & evidence

ORD record
ord-24a233adc45a427ba80f3ae2e2782bd6
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Reaction notes

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