HCID 67272021, compound → (5-Aminomethyl-2-{[(4-tert-butyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanol

HRID 251292Notes

Reaction equation

HRID 251292 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][N:12]([CH2:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=2[CH2:32][OH:33])[CH:13]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO>[NH4+:8].[OH-:33].[NH2:29][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([CH2:23][N:12]([CH2:11][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[CH:9][N:8]=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:25]([CH2:32][OH:33])[CH:26]=1

Participants

4

Reactant 1

HCID 67272021HCID 67272021, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67271580(5-Aminomethyl-2-{[(4-tert-butyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanolYield 112.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{[(4-tert-butyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzonitrile (0.153 g, 0.34 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, 90:5:5, v/v/v) afforded (5-aminomethyl-2-{[(4-tert-butyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanol as a pale yellow oil (0.085 g, 56%). 1H NMR (CDCl3) δ 1.39 (s, 9H), 1.54 (m, 1H), 1.77 (br s, 2H), 1.82 (m, 1H), 1.99 (m, 1H), 2.22 (m, 1H), 2.68 (m, 1H), 2.79 (m, 1H), 3.51 (d, 1H, J=12.0 Hz), 3.63 (dd, 2H, J=13.5, 4.5 Hz), 3.80 (s, 2H), 3.87 (m, 1H), 4.06 (d, 2H, J=12.0 Hz), 4.41 (d, 1H, J=12.0 Hz), 7.05 (dd, 1H, J=7.5, 3.0 Hz), 7.15-7.27 (m, 4H), 7.32 (d, 1H, J=9.0 Hz), 7.89 (s, 1H), 8.35 (d, 1H, J=6.0 Hz), 8.50 (d, 1H, J=3.0 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-e33e158e36974eaf95f7b93bceac7590
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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