(1-Benzylazepan-3-yl)methanol → (Azepan-3-yl)methanol

HRID 479824Notes

Reaction equation

HRID 479824 reaction equation
C([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][OH:16])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[NH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][OH:16])[CH2:9]1

Participants

4

Reactant 1

HCID 21901990(1-Benzylazepan-3-yl)methanol

Product 1

HCID 21901984(Azepan-3-yl)methanolYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

(1-Benzyl-azepan-3-yl)-methanol (144) (0.0922 g, 0.4192 mmol) dissolved in MeOH (1 mL) was added to a stirring suspension of 10% Pd/C (14.4 mg) in 5 mL MeOH. The reaction was purged with H2, and the reaction was stirred at room temperature overnight. The reaction was judged complete by 1H-NMR analysis of an aliquot from the reaction. The reaction was filtered through a pad of Celite wet with MeOH and was rinsed with MeOH, and concentrated in vacuo to obtain pure azepan-3-yl-methanol (145) in 60% yield (0.0323 g). Compound 145 was used in the next Example without further purification. 1H NMR (CDCl3, partial) 3.14-2.70 (4H, m), 1.92-1.73 (4H, m), 1.68-1.42 (3H, m) ppm. 13C NMR (CDCl3, 75 MHz) 67.32, 52.01, 50.33, 41.31, 31.05, 29.76, 25.44 ppm.

Workup

  1. customThe reaction was purged with H2
  2. customThe reaction was judged complete by 1H-NMR analysis of an aliquot from the reaction
  3. filtrationThe reaction was filtered through a pad of Celite wet with MeOH
  4. washwas rinsed with MeOH
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10bf37e7148a4fbfa6dcfd0c1fcb86e4
Source dataset
uspto-grants-2003_11
Patent number
US06645980B1

Reaction notes

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