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

HRID 1168890Notes

Reaction equation

HRID 1168890 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-d638726530a54cdea3920bb044754901
Source dataset
uspto-grants-2003_09
Patent number
US06627644B2

Reaction notes

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