4-(3,3''-Dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2'']terpyridin-1'-ylmethyl)-benzonitrile → 4-(3,3''-Dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2'']terpyridin-1'-ylmethyl)-benzylamine

HRID 1987366Notes

Reaction equation

HRID 1987366 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]2[CH2:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[N:4][CH:5]=[CH:6][CH:7]=1>N.[Ni]>[CH3:20][C:19]1[C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][CH:8]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]2[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:26][NH2:27])=[CH:28][CH:29]=2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 674219774-(3,3''-Dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2'']terpyridin-1'-ylmethyl)-benzonitrile

Product 1

HCID 674221394-(3,3''-Dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2'']terpyridin-1'-ylmethyl)-benzylamineYield 76%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

A solution of 4-(3,3″-Dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzonitrile (0.122 g, 0.32 mmol) in NH3 saturated MeOH (3 mL) was treated with Raney nickel (100 mg) and placed under 50 psi H2, on a Parr shaker, for 4 hours. The mixture was filtered through Celite and the cake was washed with MeOH. The eluant was concentrated under reduced pressure. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH) provided 93 mg (76%) of COMPOUND 68 as a white solid. 1H NMR (CDCl3) δ 1.44-1.57 (m, 1H), 1.66-1.72 (m, 2H), 1.90-2.11 (m, 3H), 2.34 (s, 6H), 3.51 (s, 2H), 3.71 (s, 2H), 3.98 (d, 2H J=10.5 Hz), 6.54 (d, 2H, J=7.8 Hz), 6.93 (d, 2H, J=7.8 Hz), 7.01 (dd, 2H, J=7.5, 4.8 Hz), 7.34 (d, 2H, J=7.5 Hz), 8.47 (d, 2H, J=3.9 Hz); ES-MS m/z 387 (M+H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe cake was washed with MeOH
  3. concentrationThe eluant was concentrated under reduced pressure
  4. customPurification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-2a12b866bba5445a92cd2dbf6354ca12
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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