Dimethylformamide → 3-(3-Cyanophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

HRID 909906Notes

Reaction equation

HRID 909906 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([N:12]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[O:11].[CH3:28][N:29](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:28]([C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([N:12]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[O:11])#[N:29]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 592904803-(3-Bromophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

Product 1

HCID 581685553-(3-Cyanophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
130 °C

Procedure

To 3-(3-bromophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide (4 g) [Preparation 3] in DMF (30 mL) was added zinc cyanide (1.59 g) and Pd(Ph3P)4 (0.52 g). The reaction flask was flushed with nitrogen then heated to 130° C. with stirring under nitrogen for 1 h. The reaction was worked up by the addition of ethyl acetate, which was washed three times with water, twice with brine, dried over sodium sulphate, filtered and the solvent removed to afford crude product as a yellow oil/gum. Further purification on silica eluting with 10-40% ethyl acetate/isohexane afforded the sub-titled compound as a pale yellow oil (3.44 g). MS [M+H-MeOH]+=357 (MultiMode+)

Workup

  1. customThe reaction flask was flushed with nitrogen
  2. additionThe reaction was worked up by the addition of ethyl acetate, which
  3. washwas washed three times with water
  4. dry with materialtwice with brine, dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto afford crude product as a yellow oil/gum
  8. customFurther purification on silica eluting with 10-40% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-4dd547100cf14e46b0d01bb936480bad
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

Loading…