Methyl Ethyl Ketone → HCID 15662589, compound

HRID 2248193Notes

Reaction equation

HRID 2248193 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH3:4].[CH2:6]([NH:8][C:9](=[O:21])[O:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[CH3:7].C([O-])(=O)C.[Na+].[BH4-].[Na+]>O.C(O)(=O)C>[CH2:6]([NH:8][C:9](=[O:21])[O:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][CH:2]([CH3:1])[CH2:3][CH3:4])=[CH:18][CH:19]=1)[CH3:7]

Participants

7

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 15662588HCID 15662588, compound

Product 1

HCID 15662589HCID 15662589, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of 2-butanone (5 ml), 2-(4-aminophenoxy)ethyl N-ethylcarbamate (1.00 g) and sodium acetate (2.50 g) in a solution of 5 ml of acetic acid and 10 ml of water, cooled to -5°, is added sodium borohydride (4.00 g) in portions. After addition is complete, the reaction mixture is adjusted to alkaline pH and is extracted with ether. The combined organic extracts are concentrated and the crude product is purified by column chromatography to give 2-[4-(1-methylpropylamino)phenoxy]ethyl N-ethylcarbamate (compound 35, Table B).

Workup

  1. temperaturecooled to -5°
  2. additionAfter addition
  3. extractionis extracted with ether
  4. concentrationThe combined organic extracts are concentrated
  5. customthe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-f60f9afa7d6e4934aaf782e06e16907a
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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