Bromine → HCID 19753486, compound

HRID 483688Notes

Reaction equation

HRID 483688 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][CH:14]([CH:18]1[CH2:20][CH2:19]1)[CH:15]1[CH2:17][CH2:16]1)[CH2:9][CH2:8]2.[Br:21]Br>CCO.C(Cl)Cl>[Br:21][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH2:8][CH2:9][CH:10]([NH:13][CH:14]([CH:18]1[CH2:20][CH2:19]1)[CH:15]1[CH2:17][CH2:16]1)[CH2:11]2

Participants

5

Reactant 2

HCID 24408BromineHCID 19753480HCID 19753480, compound

Product 1

HCID 19753486HCID 19753486, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

8-Methoxy-2-(di-cyclopropylmethylamino)tetralin (OSU427) (311 mg, 1.09 mmol) was brominated in EtOH with 1.5 ml of a solution containing 0.6 ml Br2 in 10 ml CH2Cl2). After night in room temperature, the solvent was evaporated and the raw product (HBr salt) was recrystallized from acetone/ether to give 311 mg of white crystals melting at 153°-154° C. αD20 =-51.2°. GC/MS shows M+/M+2 at m/e=363.10 (43.1%) and 365.00 (41.9%) and the base peak at m/e=160.05.

Workup

  1. waitAfter night in room temperature
  2. customthe solvent was evaporated
  3. customthe raw product (HBr salt) was recrystallized from acetone/ether

Sources & evidence

ORD record
ord-7f957e5541b14209a938e8a2dd73d759
Source dataset
uspto-grants-1993_07
Patent number
US05225596

Reaction notes

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