Hydrochloric Acid → [(2S)-2-(3,4-dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylamine dihydrochloride

HRID 749421Notes

Reaction equation

HRID 749421 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:20][CH2:21][N:22]2[CH2:25][CH:24]([N:26]3[CH2:31][CH2:30][S:29][CH2:28][CH2:27]3)[CH2:23]2)[CH2:10][N:11](C)[C:12](=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[Cl:8].[ClH:32]>CCOCC>[ClH:1].[ClH:32].[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:20][CH2:21][N:22]2[CH2:23][CH:24]([N:26]3[CH2:27][CH2:28][S:29][CH2:30][CH2:31]3)[CH2:25]2)[CH2:10][NH:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86606876tert-butyl [(2S)-2-(3,4-dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylcarbamate

Product 1

HCID 68979570[(2S)-2-(3,4-dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylamine dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl [(2S)-2-(3,4-dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylcarbamate (260 mg, 0.53 mmol) was dissolved in ether (15 mL) and stirred during the dropwise addition of HCl (15 mL of 4M dioxane solution). The mixture was stirred at room temperature for 1 h and then the solvent was removed by evaporation. There was obtained 270 mg (100%) of [(2S)-2-(3,4-dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylamine dihydrochloride as a white solid. 1H NMR (300 MHz, CD3OD): 1.9-2.2 (b, 2H), 2.7 (s, 3H), 3.0-4.8 (cm, 19H), 7.4 (d, 1H), 7.6 (m, 2H); LCMS: m/z 388 (M+1)+.

Workup

  1. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-160cb4f7171b4b9993e34af73d95aa2b
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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