Water → HCID 19822588, compound

HRID 728624Notes

Reaction equation

HRID 728624 reaction equation
[CH3:1][N:2]1[CH2:20][CH:19]2[N:5]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=32)[CH2:4][CH2:3]1.[N:21]#CBr.O>C1C=CC=CC=1.C(OCC)C>[C:1]([N:2]1[CH2:3][CH2:4][N:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH:19]2[CH2:20]1)#[N:21]

Participants

6

Reactant 3

HCID 962WaterHCID 4184MianserinHCID 10476Cyanogen Bromide

Product 1

HCID 19822588HCID 19822588, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of mianserin (5.2 g) in anhydrous benzene (20 ml) was added slowly to a stirred solution of cyanogen bromide (2.3 g) in anhydrous benzene (20 ml) in an atmosphere of nitrogen. After 24 hours, the mixture was diluted with diethyl ether (50 ml) and shaken with water (50 ml). The separated aqueous layer was back extracted with a mixture of benzene and ether (equal volumes of each, total 50 ml) and the combined organic layers dried over anhydrous potassium carbonate and then evaporated under reduced pressure. The residual solid was recrystallised from ethanol to give 2-cyanonormianserin as colourless needles m.p. 164°-166° C. This compound is outside general formula I, and was used as an intermediate only.

Workup

  1. extractionThe separated aqueous layer was back extracted with a mixture of benzene and ether (equal volumes of each, total 50 ml) and the combined organic layers
  2. dry with materialdried over anhydrous potassium carbonate
  3. customevaporated under reduced pressure
  4. customThe residual solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-3d8ff0c6c4fe498091ca8ebf9ed6013e
Source dataset
uspto-grants-1991_09
Patent number
US05049637

Reaction notes

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