Methyl Ethyl Ketone → HCID 15662589, compound

HRID 1073441Notes

Reaction equation

HRID 1073441 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-b408ea8685514ace914fa7a5d253984a
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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