Dimethylformamide → HCID 21498295, compound

HRID 1730507Notes

Reaction equation

HRID 1730507 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:13]1[C:21]2[CH:20]([CH3:22])[CH2:19][N:18]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:17][C:16]=2[CH:15]=[C:14]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].CN(C)[CH:40]=[O:41]>>[CH2:6]([N:13]1[C:21]2[CH:20]([CH3:22])[CH2:19][N:18]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:17][C:16]=2[C:15]([CH:40]=[O:41])=[C:14]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21498254HCID 21498254, compound

Product 1

HCID 21498295HCID 21498295, compound

Conditions

Temperature
50 °C

Procedure

Phosphoryl chloride (1.68 g) was added dropwise to cooled dimethyl-formamide (1.60 g). A suspension of 1,5-dibenzyl-4,5,6,7-tetrahydro-7-methyl-2-phenyl-1H-pyrrolo[3,2-c]pyridine (3.92 g) in dimethylformamide (20 ml) was added portionwise. The resulting red solution was heated at 50° C for 4 hours, allowed to cool and poured on to 250 g ice. The mixture was basified with 2N sodium hydroxide, warmed gently for a few minutes, and the solid product collected by filtration, washed with water and dried. Two recrystallisations from methanol gave 2.86 g of the title compound as white needles. M.pt. 120°-1°. (Found: C, 83.2; H, 6.9; N, 6.5. C29H28N2O requires: C, 82.8; H, 6.7; N, 6.7%).

Workup

  1. additionwas added portionwise
  2. temperatureto cool
  3. temperaturewarmed gently for a few minutes
  4. filtrationthe solid product collected by filtration
  5. washwashed with water
  6. customdried
  7. customTwo recrystallisations from methanol

Sources & evidence

ORD record
ord-5cca88676aed408cbf7af685dab0ee82
Source dataset
uspto-grants-1976_11
Patent number
US03992544

Reaction notes

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