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

HRID 720027Notes

Reaction equation

HRID 720027 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 (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 in 60% yield (0.0323 g), which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz, 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-1ce0baffe2014bde8a01a0f088b91006
Source dataset
uspto-grants-2006_11
Patent number
US07132551B2

Reaction notes

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