Chloride → HCID 14151508, compound

HRID 247439Notes

Reaction equation

[ClH:1].C[O:3][C:4]1[C:5]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][C:7]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1.N[C@H](C(O)=O)CCSC.[OH-].[NH4+].[Cl-]>CS(O)(=O)=O>[ClH:1].[OH:3][C:4]1[C:5]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][C:7]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1

Participants

Conditions

Temperature: 25 °C

Procedure

8-Methoxy-3-methyl-1-phenyl-7-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (4.5 g, 0.011 m) dissolved in methanesulfonic acid (165 ml) was treated with methionine (8.3 g, 0.055 m) and stirred for 16 hours at 25° C. The mixture was poured into ice water, basified with ammonium hydroxide and extracted with ethyl acetate. The organic phase was concentrated in vacuo and the residue purified by chromatography on silica eluted with methanol-methylene chloride (1:50) to give 8-hydroxy-3-methyl-1-phenyl-7-phenylthio-2,3,4,5-tetrahydro-1H-3-benzepine which was treated with hydrooen chloride to give 8-hydroxy-3-methyl-1-phenyl-7-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride, m.p. 175° C.

Workup

extractionextracted with ethyl acetate
concentrationThe organic phase was concentrated in vacuo
customthe residue purified by chromatography on silica
washeluted with methanol-methylene chloride (1:50)
customto give 8-hydroxy-3-methyl-1-phenyl-7-phenylthio-2,3,4,5-tetrahydro-1H-3-benzepine which

Sources & evidence

ORD record: ord-57aa1a9170a04128be4d43f6ba0476d7
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04707483

Reaction notes

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