4-(4-(Benzyl(methyl)amino)cyclohex-1-enyl)-N,N-dimethylpyridin-2-amine → N,N-Dimethyl-4-(4-(methylamino)cyclohexyl)pyridin-2-amine

HRID 1193405Notes

Reaction equation

HRID 1193405 reaction equation
[CH2:1]([N:8](C)[CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([N:21]([CH3:23])[CH3:22])[CH:16]=2)=[CH:11][CH2:10]1)C1C=CC=CC=1>CO>[CH3:22][N:21]([CH3:23])[C:17]1[CH:16]=[C:15]([CH:12]2[CH2:13][CH2:14][CH:9]([NH:8][CH3:1])[CH2:10][CH2:11]2)[CH:20]=[CH:19][N:18]=1

Participants

3

Reactant 1

HCID 667992484-(4-(Benzyl(methyl)amino)cyclohex-1-enyl)-N,N-dimethylpyridin-2-amine

Product 1

HCID 66798611N,N-Dimethyl-4-(4-(methylamino)cyclohexyl)pyridin-2-amineYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-(Benzyl(methyl)amino)cyclohex-1-enyl)-N,N-dimethylpyridin-2-amine (340 mg, 1.06 mmol, 1.0 eq.) was dissolved in MeOH (10 ml) and degassed with argon. Pd(OH)2 (170 mg) was then added and hydrogenation was carried out for 3 hours. After monitoring by TLC, the reaction mixture was filtered over Celite and the filtrate was concentrated under reduced pressure and purified by column chromatography (Alox, 2% MeOH in DCM). Yield: 71% (175 mg, 0.75 mmol)

Workup

  1. customdegassed with argon
  2. additionPd(OH)2 (170 mg) was then added
  3. filtrationthe reaction mixture was filtered over Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. custompurified by column chromatography (Alox, 2% MeOH in DCM)

Sources & evidence

ORD record
ord-7936315b2e214216afe9ce873c482b79
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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