Water → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-formylphenethoxy)propanamide

HRID 909907Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]([N:13]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:14][CH:15]([O:18][CH3:19])[O:16][CH3:17])=[O:12])#N.N1C=CC=CC=1.O.O.[PH2]([O-])=[O:38].[Na+]>C(O)(=O)C.[Ni]>[CH:20]1([N:13]([CH2:14][CH:15]([O:18][CH3:19])[O:16][CH3:17])[C:11](=[O:12])[CH2:10][CH2:9][O:8][CH2:7][CH2:6][C:5]2[CH:26]=[CH:27][CH:28]=[C:3]([CH:1]=[O:38])[CH:4]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

Conditions

Temperature: 45 °C

Procedure

To 3-(3-cyanophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide [Example 10, Step i)] (600 mg) in acetic acid (6 mL), pyridine (9 mL) and water (6 mL) was added sodium hypophosphite monohydrate (1964 mg) and Raney (R) nickel (397 mg). The reaction was heated to 45° C. under nitrogen for 2 h, then cooled to room temperature, filtered and washed with water/ethyl acetate. The filtrate was diluted with ethyl acetate, which was washed with water then dried over brine, filtered and the solvent removed. The residue was azeotroped once with ethanol to afford a light yellow oil (600 mg). MS [M+H-MeOH]+=360 (MultiMode+)

Workup

temperaturecooled to room temperature
filtrationfiltered
washwashed with water/ethyl acetate
additionThe filtrate was diluted with ethyl acetate, which
washwas washed with water
dry with materialthen dried over brine
filtrationfiltered
customthe solvent removed
customThe residue was azeotroped once with ethanol

Sources & evidence

ORD record: ord-39fb08e3b759486f9590ca61b5971660
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017602B2

Reaction notes

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