Allyl bromide → HCID 20430390, compound

HRID 2413113Notes

Reaction equation

HRID 2413113 reaction equation
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[ClH:1].[CH2:15]([N:9]1[CH2:8][CH2:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:12]=2[CH2:11][CH2:10]1)[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 117762SK&F 101055

Product 1

HCID 20430390HCID 20430390, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.52 g. of 6-chloro-2,3,4,5-tetrahydro-1H-3-benzazepine, 0.34 g. of allyl bromide, 0.6 g. of potassium carbonate and 20 ml. of 90% ethanol was stirred at room temperature for 17 hours. The mixture was filtered and the filtrate concentrated in vacuo. The residue was extracted with 35 ml. of ether and the ethereal extract treated with isopropanolic hydrogen chloride to precipitate 3-allyl-6-chloro-2,3,4,5-tetra-hydro-1H-3-benzazepine hydrochloride. Recrystallization of this salt from absolute ethanol gave 3-allyl-6-chloro-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride having a melting point of 248°-249°.

Workup

  1. additionA mixture of 0.52 g
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. extractionThe residue was extracted with 35 ml
  5. extractionof ether and the ethereal extract
  6. additiontreated with isopropanolic hydrogen chloride
  7. customto precipitate 3-allyl-6-chloro-2,3,4,5-tetra-hydro-1H-3-benzazepine hydrochloride
  8. customRecrystallization of this salt from absolute ethanol

Sources & evidence

ORD record
ord-1f97e5daafc649ff97ba3ac6d55276b7
Source dataset
uspto-grants-1985_01
Patent number
US04496558

Reaction notes

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