Naphthalene → (S)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]-thiazepine

HRID 1460488Notes

Reaction equation

HRID 1460488 reaction equation
[Na].C1C2C(=CC=CC=2)C=CC=1.CC1C=CC(S([N:22]2[CH2:26][CH2:25][CH2:24][C@H:23]2[CH2:27][N:28]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[CH2:32][S:31][C:30]3[CH:39]=[CH:40][CH:41]=[CH:42][C:29]2=3)(=O)=O)=CC=1>COCCOC>[NH:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[CH2:27][N:28]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH2:32][S:31][C:30]2[CH:39]=[CH:40][CH:41]=[CH:42][C:29]1=2

Participants

5

Reactant 3

HCID 931NaphthaleneHCID 5360545SodiumHCID 22841645(S)-5,11-Dihydro-5-(1-[4-methylphenylsulphonyl]-2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine

Product 1

HCID 22841647(S)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]-thiazepineYield 12.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Sodium (55 mg) was added to a solution of naphthalene (340 mg) in DME (6 ml) and the mixture stirred at room temperature for one hour, treated with a solution of (S)-5,11-dihydro-5-(1-[4-methylphenylsulphonyl]-2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine (see Preparations 15 and 16) (200 mg) in DME (4 ml), stirred with ice-cooling for one hour, quenched with water and extracted with ethyl acetate. The organic extract was worked-up and purified as described in Preparation 13 to give the title compound as a colourless oil, (16 mg, 12%).

Workup

  1. stirringstirred with ice-
  2. temperaturecooling for one hour
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. custompurified
  7. customas described in Preparation 13

Sources & evidence

ORD record
ord-5280579487bc46ab8b5ca5273e124cce
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

Loading…