Methylamine → 3-[8-Chloro-1-(2-fluorophenyl)-3H-2-benzazepin-5-yl]prop-2-yn-1-amine--hydrogen chloride (1/2)

HRID 464941Notes

Reaction equation

HRID 464941 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]2[C:6]([C:18]#[C:19][CH2:20][N:21]3C(=O)C4=CC=CC=C4C3=O)=[CH:7][CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1.CN>C(O)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:33]=[CH:32][C:5]2[C:6]([C:18]#[C:19][CH2:20][NH2:21])=[CH:7][CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13556894HCID 13556894, compound

Product 1

HCID 30672813-[8-Chloro-1-(2-fluorophenyl)-3H-2-benzazepin-5-yl]prop-2-yn-1-amine--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.3 g (2.9 mmoles) of 8-chloro-5-(1-phthalimido-2-propyn-3-yl)-1-(2-fluorophenyl)-3H-2-benzazepine, 50 ml of ethanol and 10 ml of 40% aqueous methylamine was stirred at room temperature for 1 hr. The mixture was poured into ice water and extracted with ether. The ether solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue was dissolved in an excess of ethanolic hydrogen chloride and the resulting salt precipitated by the addition of ether to give an off-white solid, mp 211°-216° C. Recrystallization from a mixture of methanol and ether gave gray needles, mp 216°-218° C. dec.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure to dryness
  4. dissolutionThe residue was dissolved in an excess of ethanolic hydrogen chloride
  5. customthe resulting salt precipitated by the addition of ether
  6. customto give an off-white solid, mp 211°-216° C
  7. customRecrystallization
  8. additionfrom a mixture of methanol and ether
  9. customgave gray needles, mp 216°-218° C. dec.

Sources & evidence

ORD record
ord-17d01eb0c491491cbb6db362630dd672
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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