Dichloromethane → (s)-(-)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine hydrochloride

HRID 2304396Notes

Reaction equation

HRID 2304396 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[CH2:14][N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][O:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)=[CH:5][CH:4]=1.[Cl:32]CCl>>[ClH:32].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[CH2:14][N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][O:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 15481928(S)-(-)-5,11-dihydro-5-(1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine

Product 1

HCID 70063074(s)-(-)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine hydrochlorideYield 73%

Procedure

A hydrogen chloride ether saturated solution was added to a solution of 12.0. g (23.2 mmols) of (S)-(−)-5,11-dihydro-5-(1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine in 50 ml of dichloromethane, and the mixture was stirred for 5 minutes. Then, the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from a mixed solvent of acetone and diethyl ether to give 9.5 g of (S)-(−)-5,11-dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine hydrochloride as a colorless prism crystal in a yield of 73%.

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. customThe resulting residue was recrystallized from a mixed solvent of acetone and diethyl ether

Sources & evidence

ORD record
ord-77f9e7e5a69c45988e91663bece0512b
Source dataset
uspto-grants-2002_08
Patent number
US06436922B1

Reaction notes

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