8-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine → HCID 12741416, compound

HRID 2362595Notes

Reaction equation

HRID 2362595 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:8]2>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C@H:10]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:8]2

Participants

3

Reactant 1

HCID 127414178-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 12741416HCID 12741416, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Alternatively, to a solution of 160 mg (0.72 mmol) racemic N-(8-methoxytetralin-2-yl)-N-propylamine (A2-1: R=OMe) (as the free base) in 1.0 mL EtOH were added a solution of 270 mg (0.72 mmol) of (L)-(−)-O,O-(R,R)-dibenzoyltartaric acid monohydrate in 2.0 mL EtOH and stirred for 10 min at room temperature to get a fine white precipitate, which was filtered, washed with cold ethanol and suspended in 10% (v/v) aqueous KOH. After the extraction of the aqueous layer with methylenehloride for four times the organic layers were dried over Na2SO4, the solvent was evaporated in vacuo to get (R)-N-(8-methoxytetralin-2-yl)-N-propylamine ((R)-A2-1: R=OMe).

Workup

  1. customto get a fine white precipitate, which
  2. filtrationwas filtered
  3. washwashed with cold ethanol
  4. extractionAfter the extraction of the aqueous layer with methylenehloride for four times the organic layers
  5. dry with materialwere dried over Na2SO4
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9e24db8fca4d444b9e602b216b9dbb68
Source dataset
uspto-grants-2014_04
Patent number
US08691839B2

Reaction notes

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