Water → 1-[2-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]-4-phenylpiperazine

HRID 580046Notes

Reaction equation

HRID 580046 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O[CH2:18][CH2:19][C:20]1[CH:35]=[CH:34][C:23]2[O:24][CH2:25][C:26]3[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=3[C:28](=[O:29])[C:22]=2[CH:21]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].O>CO>[O:29]=[C:28]1[C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[CH2:25][O:24][C:23]2[CH:34]=[CH:35][C:20]([CH2:19][CH2:18][N:10]3[CH2:11][CH2:12][N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:8][CH2:9]3)=[CH:21][C:22]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 108064742-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol methanesulfonate

Product 1

HCID 134771171-[2-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]-4-phenylpiperazineYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6.3 g (0.039 m) of N-phenylpiperazine, 4.32 g (0.013 m) of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol methanesulfonate of Example 1 and 1.79 g (0.013 m) of K2CO3 in 50 ml of MeOH was refluxed overnight. The reaction mixture was poured into water, extracted with CH2Cl2, dried (Na2SO4), filtered and evaporated to give the crude product (6.5 g). Two recrystallizations from absolute ethanol gave 1.63 g (32%) of crystals of 1-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]-4-phenylpiperazine, m.p. 107°-108° C.

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with CH2Cl2
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give the crude product (6.5 g)
  7. customTwo recrystallizations from absolute ethanol

Sources & evidence

ORD record
ord-b1e17d62644f4643a7697bd48bec14b7
Source dataset
uspto-grants-1988_06
Patent number
US04751238

Reaction notes

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