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

HRID 1460474Notes

Reaction equation

HRID 1460474 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:11][O:12][C:13]1[CH:41]=[CH:40][C:16]([CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][C@H:20]2[CH2:24][N:25]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH2:29][S:28][C:27]3[CH:36]=[CH:37][CH:38]=[CH:39][C:26]2=3)=[CH:15][CH:14]=1>CCOCC>[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][C@H:20]2[CH2:24][N:25]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH2:29][S:28][C:27]3[CH:36]=[CH:37][CH:38]=[CH:39][C:26]2=3)=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 9824029(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine

Product 1

HCID 67836566(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine salicylateYield 71.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of salicylic acid (800 mg) in ether (5 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) (2.50 g) in ether (10 ml) and the mixture was stirred at room temperature for 16 hours. The resulting precipitate was collected, dried and recrystallised from isopropyl acetate to give the title compound as colourless crystals, (2.35 g, 71%), m.p. 150°-151° C., [α]589 -40.6° (c=0.695 in ethanol).

Workup

  1. customThe resulting precipitate was collected
  2. customdried
  3. customrecrystallised from isopropyl acetate

Sources & evidence

ORD record
ord-24b2560581c74b028d7ea6d88a7e61f0
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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