Tert-Butylamine → HCID 71290277, compound

HRID 1944819Notes

Reaction equation

HRID 1944819 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26].[BH3-]C#N.[Na+]>C(O)C>[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH2:23][NH:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 5003444Sodium cyanoborohydrideHCID 86663391HCID 86663391, compound

Product 1

HCID 71290277HCID 71290277, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.68 g (8.43 mmol) of 6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde, 3.07 g (42.1 mmol) of tert-butylamine and 800 mg (12.7 mmol) of NaBH3CN and 100 ml of dry ethanol was stirred overnight at room temperature. The resulting mixture was evaporated to dryness, and the product was isolated by flash chromatography on silica gel 60 (40-63 um; ethyl acetate-triethylamine=20:1, vol.). Yield 1.61 g (51%) of white solid. Anal. calc. for C25H33N3: C, 79.95; H, 8.86; N, 11.19. Found: C, 80.11; H, 8.95; N, 10.95. 1H NMR (CDCl3): 8.87 (d, J=8.6 Hz, 1H, 4-H in naphthyl), 7.83 (m, 1H, 8-H in naphthyl), 7.77 (m, 1H, 4-H in Py), 7.63 (d, J=8.6 Hz, 1H, 3-H in naphthyl), 7.46 (m, 1H, 3-H in Py), 7.41 (m, 1H, 7-H in naphthyl), 7.31-7.34 (m, 2H, 5,6-H in naphthyl), 7.27 (m, 1H, 5-H in Py), 3.97 (m, 2H, NaphCH2N), 3.53 (s, 21-1, PyCH2N), 1.17 (s, 9H, PyCH2NHtBu), 0.96 (s, 9H, NaphCH2NH′Bu).

Workup

  1. customThe resulting mixture was evaporated to dryness
  2. customthe product was isolated by flash chromatography on silica gel 60 (40-63 um; ethyl acetate-triethylamine=20:1, vol.)

Sources & evidence

ORD record
ord-198c59a9ecef4700abf932998c2e2d59
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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