Hydrochloric Acid → (S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine hydrochloride

HRID 1460478Notes

Reaction equation

HRID 1460478 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:32]=[CH:31][C:7]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][S:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)=[CH:6][CH:5]=1>CCOCC>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][S:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9824029(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine

Product 1

HCID 67834802(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine hydrochlorideYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Excess saturated ethereal hydrogen chloride solution was added to a solution of (S)-5,11-dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine (see Examples 1 and 6) (1.30 g) in ether (20 ml) and the mixture was stirred at room temperature for 16 hours. The resulting precipitate was collected, washed several times with ether, dried and recrystallised from ethyl acetate to give the title compound as colourless crystals, (602 mg, 43%), m.p. 189°-190° C., [α]58925 -30.7° (c=0.57 in ethanol).

Workup

  1. customThe resulting precipitate was collected
  2. washwashed several times with ether
  3. customdried
  4. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-a5f26e2f2374407f8ce6101c199d214e
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

Loading…