Ammonia → HCID 67273307, compound

HRID 251282Notes

Reaction equation

HRID 251282 reaction equation
N.[C:2]([O:6][C:7](=[O:30])[N:8]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=1[CH2:28][OH:29])[CH:9]1[C:18]2[N:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:12][CH2:11][CH2:10]1)([CH3:5])([CH3:4])[CH3:3].[H][H]>CO.[Ni]>[C:2]([O:6][C:7](=[O:30])[N:8]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][C:21]=1[CH2:28][OH:29])[CH:9]1[C:18]2[N:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:12][CH2:11][CH2:10]1)([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 67272999HCID 67272999, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67273307HCID 67273307, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Ammonia gas was bubbled through a solution of (4-cyano-2-hydroxymethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-carbamic acid tert-butyl ester (1.39 g, 3.55 mmol) in MeOH (40 mL) for 18 minutes. A prewashed mixture of Raney Nickel (˜1 gram) was added to the nitrile and the mixture was shaken for 16 hours under 30 psi hydrogen. The mixture was filtered through a celite plug and the filtrate was concentrated under reduced pressure. Purification via column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 94:5:1, v/v/v) afforded (4-aminomethyl-2-hydroxymethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-carbamic acid tert-butyl ester as an off-white solid (0.77 g, 55%). 1H NMR (CDCl3) δ 1.05 (s, 9H), 1.76 (m, 2H), 2.25 (m, 2H), 2.67 (m, 2H), 3.85 (s, 2H), 3.92 (d, 1H, J=15.0 Hz), 4.27 (m, 1H), 4.37 (d, 1H, J=9.0 Hz), 5.02 (d, 1H, J=12.0 Hz), 5.43 (d, 1H, J=15.0 Hz), 7.00 (m, 1H), 7.19 (m, 2H), 7.22 (m, 1H), 7.45 (m, 1H), 8.14 (d, 1H, J=3.0 Hz).

Workup

  1. filtrationThe mixture was filtered through a celite plug
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification via column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 94:5:1, v/v/v)

Sources & evidence

ORD record
ord-c36e896b9dd24e48a7c7d19378527d96
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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