Benzoyl chloride → HCID 18596283, compound

HRID 1247914Notes

Reaction equation

HRID 1247914 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:14][C@H:13]3[C@@H:8]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:15][CH2:16][CH3:17])[CH2:7][C:6]=2[N:18]=1.[C:19]([Cl:27])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[ClH:27].[ClH:27].[C:19]([NH:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:14][C@H:13]3[C@@H:8]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:15][CH2:16][CH3:17])[CH2:7][C:6]=2[N:18]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 18596256HCID 18596256, compound

Product 1

HCID 18596283HCID 18596283, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the above procedure, trans-(±)-2-amino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline was reacted with benzoyl chloride in pyridine solution. The residue obtained after working up the reaction mixture as indicated above was chromatographed over florisil using chloroform with increasing amounts (0-10%) of methanol as the eluant. Fraction ten contained the desired 2-benzoylamino compound (by TLC). The solvent was removed therefrom in vacuo. The resulting residue was dissolved in ethanol and gaseous hydrogen chloride passed into the ethanol solution. Addition of ether to the point of incipient precipitation yielded trans-(±)-2-benzoylamino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline dihydrochloride; molecular ion at 350.

Workup

  1. customThe residue obtained
  2. customabove was chromatographed over florisil
  3. customThe solvent was removed
  4. dissolutionThe resulting residue was dissolved in ethanol
  5. additionAddition of ether
  6. customto the point of incipient precipitation

Sources & evidence

ORD record
ord-44f87cdabc32487091eb20c17cbf0979
Source dataset
uspto-grants-1985_06
Patent number
US04521421

Reaction notes

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