Allyl bromide → (+/-)-3-(alpha-(3,5-Dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide

HRID 1490070Notes

Reaction equation

HRID 1490070 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([CH:25]=[CH:26][CH:27]=1)[CH:10]([C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=1)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])Cl)(C)(C)C.[CH3:30][C@H:31]1[CH2:36][NH:35][CH2:34][C@@H:33]([CH3:37])[NH:32]1.[CH2:38](Br)[CH:39]=[CH2:40]>>[CH3:30][CH:31]1[NH:32][CH:33]([CH3:37])[CH2:34][N:35]([CH:10]([C:12]2[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=2)[C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16])[C:9]2[CH:25]=[CH:26][CH:27]=[C:7]([OH:6])[CH:8]=2)[CH2:36]1.[CH2:40]([N:32]1[C@@H:33]([CH3:37])[CH2:34][N:35]([CH:10]([C:12]2[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=2)[C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16])[C:9]2[CH:25]=[CH:26][CH:27]=[C:7]([OH:6])[CH:8]=2)[CH2:36][C@H:31]1[CH3:30])[CH:39]=[CH2:38]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 214803913-(3-((tert-butyldimethyl-silyl)oxy)-alpha-chlorobenzyl)-N,N-diethylbenzamide

Product 2

HCID 21480445(+/-)-3-(alpha-(3,5-Dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamideHCID 22865166(+/-)-cis-3-(alpha-(4-allyl-3,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide

Procedure

(±)-3-(α-(3,5-Dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide was prepared from 3-(3-((tert-butyldimethyl-silyl)oxy)-α-chlorobenzyl)-N,N-diethylbenzamide (Example 1, infra) and cis-2,6-dimethylpiperazine according to the methods of Example 1. This material was then alkylated with allyl bromide and deprotected by methods similar to that in Example 4 to give (±)-cis-3-(α-(4-allyl-3,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide. NMR (DMSO-d6, 200 MHz): δ 0.87 (d, J=3.9 Hz, 3H); 0.90 (d, J=3.9 Hz, 3H); 0.940-1.22 (m, 6H); 1.65 (t, J=10.7 Hz, 2H); 2.55-2.75 (m, 4H); 3.00-3.22 (m, 2H); 3.22-3.54 (m, 4H); 4.16 (s, 1H); 5.15 (dd, J1 =2.2 Hz, J2 =10.0 Hz, 1H); 5.22 (d, J=14.8 Hz, 1H); 5.96 (m, 1H); 6.58 (d, J=8.0 Hz, 1H); 6.82 (d, J=7.3 Hz, 1H); 6.84 (s, 1H); 7.02-7.20 (m, 2H); 7.30-7.46 (m, 3H); 9.33 (s, 1H). Mass spectrum (CI--CH4) m/e: 436 (M+1, 100%). The monohydrochloride salt was prepared as in Example 4. Calc. for C27H37N3O2HCl 0.75 H2O: C, 66.78; H, 8.20; N, 8.65; Cl, 7.30. Found: C, 66.84; H, 8.28; N, 8.53; Cl, 7.25.

Sources & evidence

ORD record
ord-61c64c996c4c4a1293a7176d3223fbc9
Source dataset
uspto-grants-1997_10
Patent number
US05681830

Reaction notes

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