Methane → N-benzyl-N-methylbenzamide monohydrochloride
Reaction equation
C(N1[C@H:9]([CH3:10])[CH2:8][N:7]([C@H:11]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)C([Cl:31])=O)C2C=CC=C(O[Si](C(C)(C)C)(C)C)C=2)[C@@H:6](C)C1)C=C.[CH2:36](NC)[C:37]1C=CC=[CH:39][CH:38]=1.C(N)(=[O:52])C1C=CC=CC=1.C.Cl>C(O)C>[ClH:31].[CH2:11]([N:7]([CH3:6])[C:8](=[O:52])[C:9]1[CH:10]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:26]1[CH:34]=[CH:33][CH:32]=[CH:28][CH:27]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
This compound was prepared from 3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoyl chloride and N-benzyl-N-methylamine by the Benzamide Formation Method described in Example 9. NMR (300 MHz, DMSO-d6, 121° C.): δ0.93 (d, J=6.2 Hz, 3H) 1.06 (d, J=6.2 Hz, 3H); 1.96 (dd, J1 =6.7 Hz, J2 =11.0 Hz, 1H); 2.12 (dd, J1 =7.0 Hz, J2 =11.0 Hz, 1H); 2.58 (dd, J1 =2.9 Hz, J2 =11.4 Hz, 1H); 2.67-2.84 (m, 3H); 2.86 (s, 3H); 2.89 (dd, J1 =6.6 Hz, J2 =13.5 Hz, 1H); 3.18 (dd, J1 =4.0 Hz, J2 =14.1 Hz, 1H); 4.58 (s, 2H); 4.98 (s, 1H); 5.08 (d, J=10.2 Hz, 1H); 5.16 (d, J=17.3 Hz, 1H); 5.74-5.89 (m, 1H); 6.62-6.74 (m, 3H); 7.10 (t, J=7.8 Hz, 1H); 7.21-7.50 (m, 9H); 8.76 (s, 1H). Mass spectrum (CI--CH4) m/e: 484 (M+1,88%), 330 (33%), 153 (100%). [α]D20 =+14.3° (ethanol. c=1.25). The free amine was dissolved in ethanol and titrated with ethanolic hydrogen chloride to pH 3.4 followed by precipitation with diethyl ether from dichloromethane to give (+)-3-((αR)-α-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-benzyl-N-methylbenzamide monohydrochloride as a hygroscopic light yellow powder. Calc. for C31H37N3O2HCl 0.75 H2O: C, 69.78; H, 7.46; N, 7.87; Cl, 6.64 Found: C, 69.76; H, 7.48; N, 7.69; Cl 6.74.
Workup
- customfollowed by precipitation with diethyl ether from dichloromethane
Sources & evidence
- ORD record
- ord-35cde023a38b4429912b655e926d6489
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05552404
Reaction notes
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