Hydrochloric Acid → HCID 20261344, compound

HRID 464937Notes

Reaction equation

HRID 464937 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:38]=[CH:37][C:24]2[C:25](Br)=[CH:26][CH2:27][N:28]=[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:23]=2[CH:22]=1.[CH2:39]([OH:42])[C:40]#[CH:41].Cl>[Pd](Cl)Cl.C(NCC)C>[ClH:20].[Cl:20][C:21]1[CH:38]=[CH:37][C:24]2[C:25]([C:41]#[C:40][CH2:39][OH:42])=[CH:26][CH2:27][N:28]=[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:23]=2[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 132717555-Bromo-8-chloro-1-phenyl-3H-2-benzazepine

Product 1

HCID 20261344HCID 20261344, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of 40 ml of 98% diethylamine, 44.3 mg (0.25 mmole) of palladium chloride, 131.2 mg (0.5 mmole) of triphenylphosphine, 47.6 mg (0.25 mmole) of cuprous iodide, 3.5 g (10.5 mmole) of 8-chloro-5-bromo-1-phenyl-3H-2-benzazepine and 5 ml of propargyl alcohol was stirred at room temperature under nitrogen for 7 hr. The mixture was concentrated at reduced pressure to dryness. The residue was dissolved in methylene chloride, and washed with water. The methylene chloride solution was dried over anhyrous sodium sulfate and concentrated at reduced pressure to dryness. Purification by column chromatography (silica gel, 20 g; eluent 20% ether in methylene chloride) gave a colorless oil. The oil was dissolved in an excess of methanolic hydrogen chloride and concentrated at reduced pressure to dryness. The residue crystallized from a mixture of methanol and ether to give a tan solid, mp 228°-229° C. dec.

Workup

  1. concentrationThe mixture was concentrated at reduced pressure to dryness
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialThe methylene chloride solution was dried over anhyrous sodium sulfate
  5. concentrationconcentrated at reduced pressure to dryness
  6. customPurification by column chromatography (silica gel, 20 g; eluent 20% ether in methylene chloride)
  7. customgave a colorless oil
  8. concentrationconcentrated at reduced pressure to dryness
  9. customThe residue crystallized from a mixture of methanol and ether
  10. customto give a tan solid, mp 228°-229° C. dec.

Sources & evidence

ORD record
ord-a7847ac5455040d992fbb52c925cdf35
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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