Sodium Hydroxide → HCID 20244250, compound

HRID 483012Notes

Reaction equation

HRID 483012 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]([CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:17])[CH:12]=[C:11]2[C:6]=1[CH:7]([CH2:31][CH2:32][CH:33]([OH:36])[CH2:34][CH3:35])[CH2:8][CH:9]1[CH2:30][CH2:29][CH2:28][CH2:27][N:10]12)(=O)C.OC(CC)CCC1N2C3C(CCC2CCC1)=CC=C(OC(CCCC1C=CC=CC=1)C)C=3.[OH-].[Na+]>O.N1C=CC=CC=1>[OH:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]([CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH3:17])[CH:12]=[C:11]2[C:6]=1[CH:7]([CH2:31][CH2:32][C:33](=[O:36])[CH2:34][CH3:35])[CH2:8][CH:9]1[CH2:30][CH2:29][CH2:28][CH2:27][N:10]12

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 20244273HCID 20244273, compoundHCID 86739685HCID 86739685, compound

Product 1

HCID 20244250HCID 20244250, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A solution of 5.0 g. (0.02 mole) chromic anhydride in 5.0 ml. water is added with stirring and ice cooling to 50 ml. pyridine. To this is added at 10° C., 4.93 g. (0.01 mole) dl-7acetoxy-6-(3-hydroxypentyl)-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline (prepared from dl-7-hydroxy-6-(3-hydroxypentyl-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline by the procedure of Example 62, Part A) and the resulting mixture is stirred at ambient temperature for three hours. The mixture is then poured into water, made alkaline with sodium hydroxide and extracted with methylene chloride. The combined extracts are washed with water, brine, dried (MgSO4) and the solvent evaporated in vacuo. The residue is purified by silica gel chromatography.

Workup

  1. additionTo this is added at 10° C.
  2. stirringis stirred at ambient temperature for three hours
  3. extractionextracted with methylene chloride
  4. washThe combined extracts are washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-935b868929eb4d428783b0bb5b93add0
Source dataset
uspto-grants-1986_03
Patent number
US04576964

Reaction notes

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