Water → HCID 15228232, compound

HRID 1768751Notes

Reaction equation

HRID 1768751 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[CH:7]=[CH:8][CH:9]=[C:2]12.C(N(CC)CC)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C1C=CC=CC=1>[C:17]([N:6]1[CH2:5][CH2:4][N:3]2[CH:7]=[CH:8][CH:9]=[C:2]2[CH2:1]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 15491281,2,3,4-Tetrahydropyrrolo(1,2-a)pyrazine

Product 1

HCID 15228232HCID 15228232, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 12.2 g of 1,2,3,4-tetrahydropyrrolo-[1,2-a]-pyrazine and 22.2 g of triethylamine in 50 ml of anhydrous benzene, 15.4 g of benzoyl chloride was added in small portions at 10°-15° C. The reaction mass was stirred for 3 hours at room temperature and then poured into water. The organic phase was separated, and washed with a 5% solution of sodium carbonate and then water. The solvent was removed by distillation, the residue was distilled under vacuum, and the fraction with a boiling point of 189°-191° C. at 1 mm Hg was collected. The yield of the title compound was 15 g (66.5%). Nmr (CDCl3): δ3.7-3.9 (m) (4H, 3,4-CH2); 4.58 (s) (2H, 1-CH2); 5.6-5.8 (m) (1H, 7-H); 5.8-6.0 (m) (1H, 8-H); 6.2-6.4 (m) (1H, 6 -H); 7.2-7.4 (m) (5H-C6H5). Anal. calculated for C14H14N2O: C 74.31%; H 6.24%; N 12.38% and found: C 74.21%; H 6.24%; N 12.45%.

Workup

  1. customThe organic phase was separated
  2. washwashed with a 5% solution of sodium carbonate
  3. customThe solvent was removed by distillation
  4. distillationthe residue was distilled under vacuum
  5. customthe fraction with a boiling point of 189°-191° C. at 1 mm Hg was collected

Sources & evidence

ORD record
ord-6042fce4faaf483594759a1096f9194b
Source dataset
uspto-grants-1995_01
Patent number
US05378846

Reaction notes

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