Water → HCID 14552645, compound

HRID 2309843Notes

Reaction equation

HRID 2309843 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH:11]([CH3:14])[CH2:12][NH2:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4].Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[Na+].O>CCOCC>[CH3:1][CH:2]([O:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH:11]([CH3:14])[CH2:12][NH:13][C:18](=[O:19])[O:20][CH2:21][CH3:22])=[CH:8][CH:7]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 15662567HCID 15662567, compound

Product 1

HCID 14552645HCID 14552645, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-[4-(1-methylpropoxy)phenoxy]propylamine (1.13 g, 5.10 mmol) in 25 ml of ether, at 0° and under N2, is added ethyl chloroformate (1.16 g, 10.60 mmol) by syringe, followed by addition of 10% aqueous sodium hydroxide (3.4 ml). After 15 min., the reaction is worked up by addition of water and extraction with ether. The combined organic phases are washed with 1N sulfuric acid, with water and with brine, dried and filtered, the filtrate is concentrated in vacuo and the product is purified by prep. TLC to give ethyl N-{2-[4-(1-methylpropoxy)phenoxy]propyl}carbamate.

Workup

  1. washThe combined organic phases are washed with 1N sulfuric acid, with water and with brine
  2. customdried
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customthe product is purified by prep

Sources & evidence

ORD record
ord-8d6ee46bcef4459f94cda0bd542c4f4a
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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