Diethylamine → HCID 13556888, compound

HRID 464936Notes

Reaction equation

HRID 464936 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](Br)=[CH:7][CH2:8][N+:9]([O-:17])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C(NCC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:45][N:46]([CH3:50])[CH2:47][C:48]#[CH:49]>[Pd](Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([C:49]#[C:48][CH2:47][N:46]([CH3:50])[CH3:45])=[CH:7][CH2:8][N+:9]([O-:17])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 81643N,N-DimethylpropargylamineHCID 13556886HCID 13556886, compound

Product 1

HCID 13556888HCID 13556888, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.5 g (10 mmole) of 8-chloro-5-bromo-1-phenyl-3H-2-benzazepine-2-oxide, 40 ml of 98% diethylamine, 40 ml of dimethylformamide, 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 and 16 ml of 1-dimethylamino-2-propyne was stirred at room temperature under nitrogen for 24 hr. The mixture was concentrated at reduced pressure to dryness. An ether solution of the residue containing petroleum ether was washed with water followed by dilute cold hydrochloric acid. The aqueous solution was separated, made alkaline with dilute cold sodium hydroxide and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue crystallized from a mixture of ether and petroleum ether to give a tan solid, mp 121°-123° C. Recrystallization from ether gave tan prisms, mp 124°-125° C.

Workup

  1. concentrationThe mixture was concentrated at reduced pressure to dryness
  2. additionAn ether solution of the residue containing petroleum ether
  3. washwas washed with water
  4. additionby dilute cold hydrochloric acid
  5. customThe aqueous solution was separated
  6. additionwith dilute cold sodium hydroxide
  7. extractionextracted with methylene chloride
  8. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  9. concentrationconcentrated at reduced pressure to dryness
  10. customThe residue crystallized from a mixture of ether and petroleum ether
  11. customto give a tan solid, mp 121°-123° C
  12. customRecrystallization from ether
  13. customgave tan prisms, mp 124°-125° C.

Sources & evidence

ORD record
ord-7c0f177c674349f79d6d00f9e7a5d31c
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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