Cyanogen Bromide → HCID 86734374, compound

HRID 1414537Notes

Reaction equation

HRID 1414537 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([O:27][CH3:28])[C:21]=3[S:20][C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:10][CH2:9]1)C1C=CC=CC=1.[N:29]#CBr>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([O:27][CH3:28])[C:21]=3[S:20][C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:10][CH2:9]1)#[N:29]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 86734375HCID 86734375, compound

Product 1

HCID 86734374HCID 86734374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1'-benzyl-4-methoxythioxanthene-9-spiro-4'-piperidine (15.48 g.) and cyanogen bromide (4.68 g.) in methylene chloride (155 ml.) is stirred at ambient temperature overnight. The solvent is evaporated in vacuo, the residual gum dissolved in toluene and subjected to chromatography on magnesium silicate (200 g.), eluting consecutively with petroleum ether (b.p. 60°-80° C.) (5 × 200 ml.), toluene (5 × 200 ml.) and chloroform (5 × 200 ml.). The combined chloroform fractions are evaporated in vacuo and the residual gum is triturated with ice-cold ether to give 1'-cyano-4-methoxythioxanthene-9-spiro-4'-piperidine, m.p. 145°-146° C. on recrystallisation from toluene/ether 1/2.5.

Workup

  1. customThe solvent is evaporated in vacuo
  2. dissolutionthe residual gum dissolved in toluene
  3. washeluting consecutively with petroleum ether (b.p. 60°-80° C.) (5 × 200 ml.), toluene (5 × 200 ml.) and chloroform (5 × 200 ml.)
  4. customThe combined chloroform fractions are evaporated in vacuo
  5. customthe residual gum is triturated with ice-cold ether

Sources & evidence

ORD record
ord-006d7977921042b89edfeb9cef63d7a2
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

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