Acetic Acid → HCID 21498287, compound

HRID 1730509Notes

Reaction equation

HRID 1730509 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]([CH3:17])[CH2:14][N:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][C:11]=2[CH:10]=[C:9]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]=O.Cl.CNC.O.[C:38]([OH:41])(=[O:40])[CH3:39]>>[C:38]([O:41][CH2:31][C:10]1[C:11]2[CH2:12][N:13]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:14][CH:15]([CH3:17])[C:16]=2[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:40])[CH3:39]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 21498254HCID 21498254, compound

Product 1

HCID 21498287HCID 21498287, compound

Procedure

A mixture of 1,5-dibenzyl-4,5,6,7-tetrahydro-7-methyl-2-phenyl-1H-pyrrolo[3,2-c]pyridine (2 g), formaldehyde (1 ml 40% aqueous solution) and dimethylamine hydrochloride (1 g) in glacial acetic acid (20 ml) was kept at room temperature for 3 days and then poured into water (150 ml). The mixture was extracted with ether (2 × 100 ml), the ether extracts washed with saturated sodium carbonate solution (3 × 100 ml), dried over magnesium sulphate and evaporated. Trituration of the resulting oil with ether gave the title compound as white needles. 0.82 g M.pt. 126° C(Found: C, 79.8; H, 7.1; N, 6.0. C31H30N2O2 requires: C, 80.1; H, 6.9; N, 6.0.

Workup

  1. extractionThe mixture was extracted with ether (2 × 100 ml)
  2. washthe ether extracts washed with saturated sodium carbonate solution (3 × 100 ml)
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-b952994cb4af425b96ab2b9c2feabeb1
Source dataset
uspto-grants-1976_11
Patent number
US03992544

Reaction notes

Loading…