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

HRID 1460475Notes

Reaction equation

HRID 1460475 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:9][O:10][C:11]1[CH:39]=[CH:38][C:14]([CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][C@H:18]2[CH2:22][N:23]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[CH2:27][S:26][C:25]3[CH:34]=[CH:35][CH:36]=[CH:37][C:24]2=3)=[CH:13][CH:12]=1>C(OCC)(=O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][C@H:18]2[CH2:22][N:23]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[CH2:27][S:26][C:25]3[CH:34]=[CH:35][CH:36]=[CH:37][C:24]2=3)=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 9824029(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine

Product 1

HCID 9937325(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine maleateYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of maleic acid (4.7 g) in ethyl acetate (200 ml) 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) (17.3 g) in ethyl acetate (100 ml) and the mixture was stirred at room temperature for 16 hours. The resulting precipitate was collected, dried and recrystallised from ethyl acetate/methanol to give the title compound as colourless crystals, (14.0 g, 64%), m.p. 153°-154° C., [α]58925 -39.7° (c=0.755 in ethanol).

Workup

  1. customThe resulting precipitate was collected
  2. customdried
  3. customrecrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-d280254be5ce4e318aa1adc0710c1cc8
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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