tert-Butyl {(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-fluoropiperidin-1-yl)azetidin-1-yl]butyl}methylcarbamate → {(2S)-2-(3,4-Dichlorophenyl)-4-[3-(4-fluoropiperidin-1-yl)azetidin-1-yl]butyl]methylamine dihydrochloride

HRID 749427Notes

Reaction equation

HRID 749427 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][CH:29]([F:32])[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].FC1C=CC(C(CCN2CC(N3CCSCC3)C2)CN(C)C(=O)OC(C)(C)C)=CC=1>>[ClH:1].[ClH:1].[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][CH:29]([F:32])[CH2:28][CH2:27]3)[CH2:23]2)[CH2:10][NH:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 69631586tert-Butyl {(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-fluoropiperidin-1-yl)azetidin-1-yl]butyl}methylcarbamateHCID 86606882Tert-butyl [2-(4-fluorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylcarbamate

Product 1

HCID 68981291{(2S)-2-(3,4-Dichlorophenyl)-4-[3-(4-fluoropiperidin-1-yl)azetidin-1-yl]butyl]methylamine dihydrochloride

Procedure

The compound was synthesized in an analogous way to that of Method 3e but using tert-butyl {(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-fluoropiperidin-1-yl)azetidin-1-yl]butyl}methylcarbamate rather than tert-butyl [2-(4-fluorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylcarbamate (yield, 100%). 1H NMR (500 MHz, CD3OD): 1.9-2s 2.4 (m, 6H), 2.7 (s, 3H), 3.1-5.1 (cm, 15H), 7.4 (d, 1H), 7.7 (m, 2H), LCMS: m/z 389 (M+1)+.

Workup

  1. customThe compound was synthesized in an analogous way to that of Method 3e

Sources & evidence

ORD record
ord-3377470b112a4eb2abdeebd779bc2a90
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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