Cyanogen Bromide → HCID 9795239, compound

HRID 1591043Notes

Reaction equation

HRID 1591043 reaction equation
[N:1]#[C:2]Br.[C:4]1([CH:10]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][NH:14][CH2:13][CH2:12][NH:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[C:4]1([CH:10]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]([C:2]#[N:1])[CH2:13][CH2:12][NH:11]2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 13279663HCID 13279663, compound

Product 1

HCID 9795239HCID 9795239, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 6.87 g (63 mmol) of cyanogen bromide in 15 mL of methanol was added to a solution of 15 g (63 mmol) of 1,2,3,4,5,6-hexahydro-1-phenyl-2,5-benzodiazocine in 110 mL of methanol at 0°. The reaction was allowed to come to room temperature and stirred 3 hours. The reaction was stripped and the residue partitioned between ethyl acetate and water made slightly acidic with 6N HCl. The aqueous layer was made basic, extracted into ethyl acetate, dried, stripped and chromatographed on ten times its weight of silica gel, eluting with 1:9 ethyl acetate/dichloromethane. There was obtained 5.93 g of 6-phenyl-3,4,5,6-tetrahydro-2,5-benzodiazocine-2(1H)-carbonitrile, mp 134°-135° from dichloromethane/ether/hexane.

Workup

  1. customto come to room temperature
  2. customthe residue partitioned between ethyl acetate and water
  3. extractionextracted into ethyl acetate
  4. customdried
  5. customchromatographed on ten times its weight of silica gel
  6. washeluting with 1:9 ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-5d0e9bff3a094a13a997fbd19886f236
Source dataset
uspto-grants-1993_04
Patent number
US05206231

Reaction notes

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