Propylamine → (7-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine

HRID 983484Notes

Reaction equation

HRID 983484 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=O)[CH2:9]2)=[CH:4][CH:3]=1.[CH2:13]([NH2:16])[CH2:14][CH3:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([NH:16][CH2:13][CH2:14][CH3:15])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 36915747-Bromo-2-tetraloneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17932068(7-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 7-bromo-3,4-dihydro-1H-naphthalen-2-one, prepared as described in J. Med. Chem, 1993, 36, 2279-2291, (5.2 g, 23 mmol) in 1,2 dichloroethane (30 mL), propyl amine (1.63 g, 28 mmol) was added, followed by addition of sodium triacetoxyborohydride (7.3 g, 34.5 mmol). The reaction was stirred at ambient temperature under nitrogen for 24 h, 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 to yield (7-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine (2.75 g).

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

Sources & evidence

ORD record
ord-e0851b5c1b534660affc10d2648a310a
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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