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

HRID 1460476Notes

Reaction equation

HRID 1460476 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:36]=[CH:35][C:11]([CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[CH2:19][N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][S:23][C:22]3[CH:31]=[CH:32][CH:33]=[CH:34][C:21]2=3)=[CH:10][CH:9]=1>ClCCl>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[CH2:19][N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][S:23][C:22]3[CH:31]=[CH:32][CH:33]=[CH:34][C:21]2=3)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 9824029(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine

Product 1

HCID 88452751(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine methanesulphonateYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonic acid (39 mg) 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) (175 mg) in dichloromethane (5 ml) and the mixture was stirred at room temperature for 16 hours and evaporated under reduced pressure. The residue was crystallised from ethyl acetate/diisopropyl ether to give the title compound as colourless crystals, (150 mg, 31%), m.p. 118°-122° C., [α]58925 -36.9° (c=0.59 in ethanol).

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was crystallised from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-71a82233e1a1419aa062770e9915adcd
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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