Water → HCID 86734687, compound

HRID 329019

Reaction equation

HRID 329019 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH2:5]1[C@@H:15]2[C@H:9]([CH:10]=[CH:11][C:12]3[C:13]4[N:14]2[C:16]2[CH:25]=[CH:24][N:23]=[CH:22][C:17]=2[C:18]=4[CH2:19][CH2:20][CH:21]=3)[CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.O>CN(C=O)C>[CH2:3]([CH:7]1[CH2:8][CH:9]2[CH:10]=[CH:11][C:12]3[C:13]4[N:14]([C:16]5[CH:25]=[CH:24][N:23]=[CH:22][C:17]=5[C:18]=4[CH2:19][CH2:20][CH:21]=3)[CH:15]2[CH2:5][CH2:6]1)[C:2]#[CH:1]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 8471TriethylamineHCID 86734686(+/-)-trans-1,2,3,4,4a,8,9,14a-Octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine

Product 1

HCID 86734687HCID 86734687, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propargyl bromide, 2.38 g, was added to a solution of (±)-trans-1,2,3,4,4a,8,9,14a-octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine (5.52 g) and triethylamine (3ml) in 90 ml DMF. The reaction mixture was stirred at room temperature for 41/2 hours. Some precipitate had formed. The reaction mixture was poured into 300 ml of cold water. A solid precipitated which was filtered off and washed with cold water. Recrystallization from 300 ml ethanol gave 4.05 g of the title compound as pale yellow needles, m.p. 160°-161.5°. An analytical sample was recrystallized again from ethanol to give almost colorless needles, m.p. 162°-163° C.

Workup

  1. customSome precipitate had formed
  2. customA solid precipitated which
  3. filtrationwas filtered off
  4. washwashed with cold water
  5. customRecrystallization from 300 ml ethanol

Sources & evidence

ORD record
ord-2267185dc3a940659d582e0f62c4f13d
Source dataset
uspto-grants-1977_04
Patent number
US04018930

Linked notes

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