6-[(4-Fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane → 6-[(4-Fluoro-3-methylphenoxy)methyl]-2-methylazepane

HRID 467480Notes

Reaction equation

[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH2:7][CH:8]2[CH2:14][N:13](CC3C=CC=CC=3)[CH:12]([CH3:22])[CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[CH3:25]>[OH-].[OH-].[Pd+2].CO>[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH2:7][CH:8]2[CH2:14][NH:13][CH:12]([CH3:22])[CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[CH3:25]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 6-[(4-fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane (2-6, 250 mg, 0.74 mmol, 1.0 equiv) and Pearlman's catalyst (wet 20% Pd(OH)2/C) (78 mg, 0.11 mmol, 0.15 equiv) in methanol (30 mL) was stirred under a hydrogen balloon for 1 hour at 23° C. The suspension was filtered and the filtrate was concentrated to give 6-[(4-fluoro-3-methylphenoxy)methyl]-2-methylazepane (2-7). δ 6.90 (m, 1H), 6.71 (m, 2H), 3.72-1.75 (m, 19H). LRMS m/z (M+H) 252.3 found, 252.2 required.

Workup

filtrationThe suspension was filtered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-9398a3c4111740d38ee96b32fe409e58
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623863B2

Reaction notes

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