Propylamine → 19485-87-1

HRID 2301394Notes

Reaction equation

HRID 2301394 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=O.[CH2:12]([NH2:15])[CH2:13][CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:12]([NH:15][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 682662-TetraloneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 1833174319485-87-1

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3,4-dihydro-1-H-naphthalen-2-one (5 g, 34 mmol) in 1,2-dichloroethane (250 mL), propyl amine (2.8 mL, 34 mmol) was added, followed by addition of sodium triacetoxyborohydride (22 g, 102 mmol). The reaction was stirred at ambient temperature under nitrogen for 24 hours, at which time it was concentrated in vacuo. The remaining solid was partitioned between 1 M sodium hydroxide and ethyl acetate. The ethyl acetate was washed with brine, dried over magnesium sulfate, and filtered. The filtrate was acidified with 1 M HCl in ether and 6.3 g of propyl-(1,2,3,4-tetrahydro-naphthalen-2-yl)-amine was collected as a pale pink precipitate.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe remaining solid was partitioned between 1 M sodium hydroxide and ethyl acetate
  3. washThe ethyl acetate was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customwas collected as a pale pink precipitate

Sources & evidence

ORD record
ord-f9ef28ceb3a243078e236501c7e5f9c6
Source dataset
uspto-grants-2002_12
Patent number
US06500822B2

Reaction notes

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