6-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-azepine hydrochloride → 3-(4-Methoxyphenyl)azepane hydrochloride

HRID 1507177Notes

Reaction equation

HRID 1507177 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH:16]=2)=[CH:6][CH:5]=1>CO.[Pd]>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16]2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 1182075626-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-azepine hydrochloride

Product 1

HCID 1178583523-(4-Methoxyphenyl)azepane hydrochlorideYield 66.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-azepine hydrochloride (0.3 g, 1.251 mmol) and 10% Pd-C (0.133 g, 1.251 mmol) in methanol (5 mL), was hydrogenated at 50 psi for 12 h. The reaction mixture was filtered through Celite and and concentrated to yield crude 3-(4-methoxyphenyl)azepane hydrochloride (0.2 g, 57%) as a black gum, used without further purification. LCMS: RT 0.62 min. LCMS (ES-API), m/z 206.1 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f5e1f9539281401892229fbd59858835
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

Loading…