Ammonia → HCID 15228235, compound

HRID 1768752Notes

Reaction equation

HRID 1768752 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH2:8]=O.[C:10]([N:18]1[CH2:23][CH2:22][N:21]2[CH:24]=[CH:25][CH:26]=[C:20]2[CH2:19]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N>O>[C:10]([N:18]1[CH2:23][CH2:22][N:21]2[C:24]([CH2:8][N:2]3[CH2:7][CH2:6][O:5][CH2:4][CH2:3]3)=[CH:25][CH:26]=[C:20]2[CH2:19]1)(=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 197884Morpholine, hydrochloride (1:1)HCID 15228232HCID 15228232, compound

Product 1

HCID 15228235HCID 15228235, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.05 g of morpholine hydrochloride, 1.24 g of a 40% solution of formaldehyde, and 3.4 g of 2-benzoyl-1,2,3,4-tetrahydropyrrolo-[1,2-a]-pyrazine was stirred for 4 hours at room temperature. 10 ml of water, alkalized with a 25% solution of ammonia, was added to the reaction mass and the product was extracted with benzene. The benzene solution was filtered through a column of aluminium oxide and the benzene was removed by distillation to give 2.2 g (67.5%) of 2-benzoyl-6-(morpholinomethyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine. This compound was prepared in the form of a noncrystalline oil. Nmr (CDCl3): δ2.1-2.4 (m) (4H, CH2); 3.3 (s) (2H, CH2N); 3.5-3.6 (m) (4H, CH2); 3.7-4.0 (m) (4H, 3,4-CH2); 4.6 (s) (2H, 1-CH2); 5.6-5.7 (m) (1H, 7-H); 5.8-5.9 (m) 1H, 8H); 7.3-7.4 (5H, C6H5). Anal. calculated for C19H23N3O2 : C 70.13%; H 7.12%; N 12.91% and found: C 70.36%; H 7.19%; N 12.75%.

Workup

  1. additionwas added to the reaction mass
  2. extractionthe product was extracted with benzene
  3. filtrationThe benzene solution was filtered through a column of aluminium oxide
  4. customthe benzene was removed by distillation

Sources & evidence

ORD record
ord-f23cf8cc657f472f9ace3a33adbd0e49
Source dataset
uspto-grants-1995_01
Patent number
US05378846

Reaction notes

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