Dimethylformamide → HCID 68128747, compound

HRID 1077049Notes

Reaction equation

HRID 1077049 reaction equation
[CH2:1]1[C:11]2[N:10]3[C:12]4[CH:21]=[CH:20][N:19]=[CH:18][C:13]=4[C:14]4[CH2:15][CH2:16][CH:17]=[C:8]([C:9]=43)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH2:2]1.Br[CH2:23][CH:24]=[CH2:25].C(=O)(O)[O-].[Na+].CN(C)C=O>O>[CH2:25]([CH:3]1[CH2:4][C:5]2[CH:6]=[CH:7][C:8]3[C:9]4[N:10]([C:12]5[CH:21]=[CH:20][N:19]=[CH:18][C:13]=5[C:14]=4[CH2:15][CH2:16][CH:17]=3)[C:11]=2[CH2:1][CH2:2]1)[CH:24]=[CH2:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 67838308HCID 67838308, compound

Product 1

HCID 68128747HCID 68128747, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.3 g. of the product of Example 1, 1.45 g. of freshly distilled 3-bromopropene and 1.7 g. of sodium bicarbonate is stirred at room temperature, for 24 hours, in 50 ml. dimethylformamide. At the end of this period, the mixture is poured into water, extracted with ether, and the combined extracts are dried and stripped down. The residue is dissolved in benzene, and the resulting solution chromatographed through a column of neutral alumina. The oily residue obtained on stripping down the eluate is recrystallized from isopropyl alcohol to yield 3-allyl-1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine m.p. 112°-113°.

Workup

  1. additionA mixture of 3.3 g
  2. extractionextracted with ether
  3. customthe combined extracts are dried
  4. dissolutionThe residue is dissolved in benzene
  5. customthe resulting solution chromatographed through a column of neutral alumina
  6. customThe oily residue obtained
  7. customis recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-067d6eb5f37344f69c32f58c564d32ca
Source dataset
uspto-grants-1976_05
Patent number
US03959300

Reaction notes

Loading…