Water → 3-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amine

HRID 410149Notes

Reaction equation

HRID 410149 reaction equation
Cl.[Cl:2][CH:3]=[CH:4][CH2:5][NH:6][C@@H:7]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:8].[OH-].[Na+].O>CO>[Cl:2][CH:3]=[CH:4][CH2:5][NH:6][C@@H:7]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 866746013-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amine hydrochloride

Product 1

HCID 866746003-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amineYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The pH of the solution of 3-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amine hydrochloride (50 g) in methanol (500 mL) was adjusted to 11 to 12 using aqueous sodium hydroxide solution (˜20% w/v) at room temperature. De-ionized water (500 ml) was added to the solution. The mixture was extracted with dichloromethane (250 mL). Layers were separated and the aqueous layer was re-extracted with dichloromethane (125 mL). The combined organic layers were washed with de-ionized water (2×250 mL) and concentrated under vacuum at 35° C. to 40° C. to give 3-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amine as oil.

Workup

  1. extractionThe mixture was extracted with dichloromethane (250 mL)
  2. customLayers were separated
  3. extractionthe aqueous layer was re-extracted with dichloromethane (125 mL)
  4. washThe combined organic layers were washed with de-ionized water (2×250 mL)
  5. concentrationconcentrated under vacuum at 35° C. to 40° C.

Sources & evidence

ORD record
ord-1fe6ddbcb60244c5b643d689eb4ab677
Source dataset
uspto-grants-2014_06
Patent number
US08759586B2

Reaction notes

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