Acetaldehyde → HCID 19769367, compound

HRID 1590048Notes

Reaction equation

HRID 1590048 reaction equation
Cl.[NH2:2][C:3]1[C:4]([Cl:24])=[CH:5][C:6]2[C:7](=[O:23])[N:8]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:9](=[O:16])[C:10]3[C:15]=2[C:14]=1[CH:13]=[CH:12][CH:11]=3.[CH:25](=O)[CH3:26].C([BH3-])#N.[Na+]>CO.O>[NH2:2][C:3]1[C:4]([Cl:24])=[CH:5][C:6]2[C:7](=[O:23])[N:8]([CH:17]3[CH2:18][CH2:19][N:20]([CH2:25][CH3:26])[CH2:21][CH2:22]3)[C:9](=[O:16])[C:10]3[C:15]=2[C:14]=1[CH:13]=[CH:12][CH:11]=3

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydride2×HCID 19769421HCID 19769421, compound

Product 1

HCID 19769367HCID 19769367, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-amino-5-chloro-2,3-dihydro-2-(piperidin-4-yl)-1H-benz[de]isoquinoline-1,3-dione hydrochloride (0.9 g; 2.46 mmol), prepared as in Example 10, in methanol (30 mL) and water (5 mL), was added acetaldehyde (2 mL) and sodium cyanoborohydride (approximately 0.5 g) and the reaction mixture stirred for two hours. Additional sodium cyanoborohydride (0.4 g) was added and the mixture stirred for an additional 2 hours. The solution was concentrated to a small volume, acidified with concentrated hydrochloric acid, and then digested for 16 hours. Solid potassium carbonate was added and the solution was extracted twice with methylene chloride. The extracts were combined, dried over potassium carbonate, and concentrated. Purification by column chromatography (silica gel; 3% methanol in CH2Cl2 and approximately 1% NH4OH) gave 6-amino-5-chloro-2-(1-ethylpiperidin-4-yl)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione (0.6 g; 1.68 mmol).

Workup

  1. stirringthe mixture stirred for an additional 2 hours
  2. concentrationThe solution was concentrated to a small volume
  3. waitdigested for 16 hours
  4. additionSolid potassium carbonate was added
  5. extractionthe solution was extracted twice with methylene chloride
  6. dry with materialdried over potassium carbonate
  7. concentrationconcentrated
  8. customPurification by column chromatography (silica gel; 3% methanol in CH2Cl2 and approximately 1% NH4OH)

Sources & evidence

ORD record
ord-72aed68d49be46f9820ddaaa51e77181
Source dataset
uspto-grants-1993_04
Patent number
US05202318

Reaction notes

Loading…