HCID 67422644, compound → HCID 67420317, compound

HRID 1784222Notes

Reaction equation

HRID 1784222 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][N:12]1[CH:17]([C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][N:19]=2)[CH2:16][CH2:15][CH2:14][CH:13]1[C:26]1[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][N:27]=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]2[CH:13]([C:26]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][N:27]=3)[CH2:14][CH2:15][CH2:16][CH:17]2[C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][N:19]=2)=[C:3]([CH2:2][OH:1])[CH:4]=1

Participants

4

Reactant 1

HCID 67422644HCID 67422644, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67420317HCID 67420317, compoundYield 196%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-hydroxymethyl-4-(3,5,3″,5″-tetramethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzonitrile (0.060 g, 0.14 mmol) dissolved in MeOH (7 mL) ammonia gas was bubbled for 10 minutes. A pre-washed mixture of Raney Nickel (˜0.5 gram) was added to the nitrile and the mixture was shaken on the hydrogenator at 40 psi for 2 hours. The mixture was filtered through a sintered glass funnel containing a celite plug and the filtrated was concentrated in vacuo to give a green foam. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 87:8:5, v/v/v) afforded [5-aminomethyl-2-(3,5,3″,5″-tetramethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-phenyl]-methanol as a pale yellow foam (0.061 g, 99%). 1H NMR (CDCl3) δ 1.52-1.62 (m, 3H), 1.98 (m, 1H), 2.10 (s, 6H), 2.20-2.30 (m, 2H), 2.37 (s, 6H), 3.50 (s, 2H), 3.57 (s, 1H), 3.88 (d, 2H, J=9.0 Hz), 4.27 (s, 2H), 6.59 (d, 1H, J=9.0 Hz), 6.68 (d, 1H, J=9.0 Hz), 6.89 (s, 1H), 7.03 (s, 2H), 8.03 (s, 2H).

Workup

  1. customwas bubbled for 10 minutes
  2. additionA pre-washed mixture of Raney Nickel (˜0.5 gram)
  3. additionwas added to the nitrile
  4. filtrationThe mixture was filtered through a sintered glass funnel
  5. additioncontaining a celite plug
  6. concentrationthe filtrated was concentrated in vacuo
  7. customto give a green foam
  8. customPurification by column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record
ord-bbe1a5193e8f44d29aac70cb11d77962
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

Loading…