HCID 67271631, compound → HCID 67271657, compound

HRID 1592692Notes

Reaction equation

HRID 1592692 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][N:12]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][N:25]=1)[CH:13]1[C:22]2[N:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:16][CH2:15][CH2:14]1)[C:6]#[N:7]>CO>[NH4+:7].[OH-:1].[NH2:7][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([CH2:11][N:12]([CH2:23][C:24]2[CH:29]=[C:28]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:27]=[CH:26][N:25]=2)[CH:13]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)=[C:3]([CH2:2][OH:1])[CH:4]=1

Participants

4

Reactant 1

HCID 67271631HCID 67271631, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67271657HCID 67271657, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-hydroxymethyl-4-{[(4-phenyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzonitrile (0.183 g, 0.40 mmol) dissolved in MeOH (8 mL) NH3 gas was bubbled for 10 minutes. A prewashed mixture of Raney Nickel (˜1 gram) was added to the nitrile and the mixture was shaken on the hydrogenator at 35 psi for 2 hours. The mixture was filtered through a sintered glass funnel containing a celite plug and the filtrate was concentrated in vacuo to a pale yellow oil. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 87:8:5, v/v/v) afforded (5-aminomethyl-2-{[(4-phenyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanol as a colorless oil (0.036 g, 19%). 1H NMR (CDCl3) δ 1.61 (m, 1H), 1.92-2.05 (m, 2H), 2.29 (m, 1H), 2.66 (m, 1H), 2.79 (m, 1H), 3.60 (d, 1H, J=12.0 Hz), 3.68-3.81 (m, 4H), 3.93 (m, 1H), 4.08 (m, 3H), 4.49 (d, 1H), 7.01 (dd, 1H, J=7.5, 3.0 Hz), 7.16 (d, 1H, J=7.5 Hz), 7.24-7.30 (m, 3H), 7.44 (m, 2H), 7.57 (t, 2H, J=7.5 Hz), 7.92 (d, 2H, J=6.0 Hz), 8.11 (s, 1H), 8.47 (d, 1H, J=3.0 Hz), 8.50 (d, 1H, J=4.5 Hz).

Workup

  1. customwas bubbled for 10 minutes
  2. additionA prewashed mixture of Raney Nickel (˜1 gram)
  3. additionwas added to the nitrile
  4. filtrationThe mixture was filtered through a sintered glass funnel
  5. additioncontaining a celite plug
  6. concentrationthe filtrate was concentrated in vacuo to a pale yellow oil
  7. customPurification by column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record
ord-57e4def3b593486da1baf6e85b5edb1c
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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