Ammonia → (2-Aminomethyl-4-methoxy-benzyl)-(3-methyl-pyridin-2-ylmethyl)-(1-pyridin-2-yl-ethyl)-amine

HRID 1592653Notes

Reaction equation

HRID 1592653 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:11][N:12]([CH2:21][C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH3:14])=[C:7]([CH:10]=1)[C:8]#[N:9].N>CO.[Ni]>[NH2:9][CH2:8][C:7]1[CH:10]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[CH2:11][N:12]([CH2:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][N:23]=1)[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:14]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 672723475-Methoxy-2-{[(3-methyl-pyridin-2-ylmethyl)-(1-pyridin-2-yl-ethyl)-amino]-methyl}-benzonitrile

Product 1

HCID 58997105(2-Aminomethyl-4-methoxy-benzyl)-(3-methyl-pyridin-2-ylmethyl)-(1-pyridin-2-yl-ethyl)-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of the above nitrile (258 mg, 0.69 mmol) in MeOH saturated with NH3 (15 mL) was hydrogenated (40 psi) over Raney-nickel for 4 hours. The mixture was filtered with suction through a pad of celite, washing with excess MeOH. The filtrate was concentrated under reduced pressure, giving the crude amine as a purple foam.

Workup

  1. customfor 4 hours
  2. filtrationThe mixture was filtered with suction through a pad of celite
  3. washwashing with excess MeOH
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-22d1a696ec6a4f978aac700798b683dd
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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