Methane → HCID 67729068, compound

HRID 1490069Notes

Reaction equation

HRID 1490069 reaction equation
[CH2:1]([N:4]1[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:29]([Cl:31])=[O:30])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si](C(C)(C)C)(C)C)[CH:13]=2)[C@@H:6]([CH3:35])[CH2:5]1)[CH:2]=[CH2:3].[CH2:36]([NH:43][CH3:44])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N)(=O)C1C=CC=CC=1.C.Cl>C(O)C>[ClH:31].[CH2:1]([N:4]1[CH: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:29]([N:43]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH3:44])=[O:30])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[C@@H:6]([CH3:35])[CH2:5]1)[CH:2]=[CH2:3]

Participants

7

Reactant 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 2331BenzamideHCID 7669N-MethylbenzylamineHCID 111350383-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoyl chloride

Product 1

HCID 67729068HCID 67729068, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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.): δ 0.93 (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,SR)-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

  1. customfollowed by precipitation with diethyl ether from dichloromethane

Sources & evidence

ORD record
ord-80e26fe63412435a890bb0204db6b5a5
Source dataset
uspto-grants-1997_10
Patent number
US05681830

Reaction notes

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