Ammonium Hydroxide → HCID 18635434, compound

HRID 2352320Notes

Reaction equation

HRID 2352320 reaction equation
[ClH:1].[CH2:2]([N:5]([CH2:19][CH2:20][CH3:21])[C@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:16]C)[C@H:7]1[CH3:18])[CH:3]=[CH2:4].B(Br)(Br)Br.[NH4+].[OH-]>C(Cl)(Cl)Cl>[ClH:1].[CH2:2]([N:5]([CH2:19][CH2:20][CH3:21])[C@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[OH:16])[C@H:7]1[CH3:18])[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 67822515HCID 67822515, compound

Product 1

HCID 18635434HCID 18635434, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The intermediate cis-N-allyl-5-methoxy-1-methyl-2-(n-propylamino) tetralin hydrochloride (20 mg; 0.68 mmol) was dissolved in CHCl3 (2 ml) and added during 2 minutes to a well-stirred solution of BBr3 (1.10 g; 4.39 mmol) in CHCl3 (13 ml) maintained in the temperature range 23°-26° C. The stirring was continued for 15 minutes at 20° C. The reaction mixture was poured into a well-stirred mixture of ice (6 g) and concentrated NH4OH (1.5 ml). The two-phase system was kept at 0° for 30 minutes with continuous stirring. The system was separated and the organic phase was dried and evaporated. The desired oily product was precipitated as a hydrochloride salt and was recrystallized from CHCl3 /ether.

Workup

  1. temperaturemaintained in the temperature
  2. customrange 23°-26° C
  3. waitThe two-phase system was kept at 0° for 30 minutes with continuous stirring
  4. customThe system was separated
  5. customthe organic phase was dried
  6. customevaporated
  7. customThe desired oily product was precipitated as a hydrochloride salt
  8. customwas recrystallized from CHCl3 /ether

Sources & evidence

ORD record
ord-8526908e913b40fc90021ed6786eaae5
Source dataset
uspto-grants-1989_10
Patent number
US04876284

Reaction notes

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