Hydrochloric Acid → HCID 70498770, compound

HRID 464939Notes

Reaction equation

HRID 464939 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:20]=[CH:19][C:6]2[C:7](Br)=[CH:8][CH2:9][N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1.[CH3:21][NH:22][CH2:23][C:24]#[CH:25].Cl>C(NCC)C.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:20]=[CH:19][C:6]2[C:7]([C:25]#[C:24][CH2:23][NH:22][CH3:21])=[CH:8][CH2:9][N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 96160N-methylpropyn-2-ylamineHCID 132717565-Bromo-8-chloro-1-phenyl-3H-2-benzazepine--hydrogen chloride (1/1)

Product 1

HCID 70498770HCID 70498770, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8021DiethylamineSolvent

Procedure

A mixture of 3.7 g (10 mmole) of 8-chloro-5-bromo-1-phenyl-3H-2-benzazepine hydrochloride, 0.4 g (0.6 mmole) of dichlorobis(triphenylphosphine)palladium (II), 0.2 g (1 mmole) cuprous iodide and 2 ml (excess) of 97% N-methylpropargylamine in 50 ml of 98% diethylamine and 100 ml of methylene chloride was stirred at room temperature under nitrogen for 24 hr. The reaction was concentrated at reduced pressure to dryness. The residue was dissolved in methylene chloride and extracted with dilute ice cold hydrochloric acid. The acid extract was made alkaline with dilute ice cold sodium carbonate and extracted with ether. The ether solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. Purification of the residue by column chromatography (silica gel, 20 g; eluent, 20% ether in methylene chloride followed by 10% methanol in methylene chloride) gave from the latter eluent an amber oil. The oil was dissolved in an excess of methanolic hydrogen chloride and concentrated at reduced pressure to dryness. The residue crystallized from isopropanol to give end product which when recrystallized from isopropanol gave tan crystals, mp 169°-175° C. dec.

Workup

  1. concentrationThe reaction was concentrated at reduced pressure to dryness
  2. dissolutionThe residue was dissolved in methylene chloride
  3. extractionextracted with dilute ice cold hydrochloric acid
  4. extractionThe acid extract
  5. extractionextracted with ether
  6. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure to dryness
  8. customPurification of the residue by column chromatography (silica gel, 20 g; eluent, 20% ether in methylene chloride followed by 10% methanol in methylene chloride)
  9. customgave from the latter eluent an amber oil
  10. concentrationconcentrated at reduced pressure to dryness
  11. customThe residue crystallized from isopropanol
  12. customto give end product which when
  13. customrecrystallized from isopropanol
  14. customgave tan crystals, mp 169°-175° C. dec.

Sources & evidence

ORD record
ord-dd929575750949ee87e5b2a105be768b
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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