Sodium Hydroxide → HCID 26778945, compound

HRID 1836316Notes

Reaction equation

HRID 1836316 reaction equation
[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[C:13]1([CH3:22])[C:14]([C:19](Cl)=[O:20])=[CH:15][CH:16]=[CH:17][CH:18]=1>ClCCl>[CH3:22][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([NH:9][CH2:8][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:10])=[O:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 702762-Methylbenzoyl chlorideHCID 1547949(R)-(+)-beta-Methylphenethylamine

Product 1

HCID 26778945HCID 26778945, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-2-phenylpropyl amine (1.24 g; 9.17 mmol), 1N NaOH (20 mL), and dichloromethane (20 mL) is treated with o-toluoyl chloride (1.42 g; 9.17 mmol) added dropwise; the mixture is then stirred at room temperature for 1 hour. The phases are separated and the aqueous layer extracted with dichloromethane (2×70 ml). The combined extracts are washed with water (1×30 mL) and brine (1×30 mL), dried over magnesium sulfate, and evaporated to give the product as a white solid.

Workup

  1. additionadded dropwise
  2. customThe phases are separated
  3. extractionthe aqueous layer extracted with dichloromethane (2×70 ml)
  4. washThe combined extracts are washed with water (1×30 mL) and brine (1×30 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-5958240cdbcf4c53a1f8bccb8867e84d
Source dataset
uspto-grants-2004_08
Patent number
US06777422B2

Reaction notes

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