Hydrochloric Acid → 3-(3-Bromophenethoxy)-N-cyclohexyl-N-(2-oxoethyl)propanamide

HRID 909884Notes

Reaction equation

HRID 909884 reaction equation
[Br:1][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](OC)[O:15]C)=[O:11].Cl>CC(C)=O>[Br:1][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[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[CH2:13][CH:14]=[O:15])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 592904803-(3-Bromophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

Product 1

HCID 592903843-(3-Bromophenethoxy)-N-cyclohexyl-N-(2-oxoethyl)propanamideYield 111.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-(3-bromophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide (1.5 g) in acetone (30 mL) was added 2M hydrochloric acid (15 mL). The mixture was stirred for 2 h before the solvent was removed under vacuum, followed by the addition of water. The aqueous phase was extracted three times with DCM and the pooled DCM was washed once with brine, dried over sodium sulphate, filtered and the solvent removed to afford the desired material (1.5 g). This material was used in the next step directly.

Workup

  1. customwas removed under vacuum
  2. additionfollowed by the addition of water
  3. extractionThe aqueous phase was extracted three times with DCM
  4. washthe pooled DCM was washed once with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent removed

Sources & evidence

ORD record
ord-66d802a35e93430992897210d04b6bef
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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