Acetic Acid → HCID 70203387, compound

HRID 617230Notes

Reaction equation

HRID 617230 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C@H:14]([NH2:16])[CH3:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[ClH:1].[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C@H:14]([NH:16][CH2:23][C:22]3[CH:25]=[CH:26][C:19]([N:18]([CH3:27])[CH3:17])=[CH:20][CH:21]=3)[CH3:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 4311764Sodium borohydrideHCID 53794912HCID 53794912, compound

Product 1

HCID 70203387HCID 70203387, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.35 g of (2R)-N1 -(7-chloro-quinolin-4-yl)-propane-1,2-diamine (see Example 118) and 0.22g of 4-dimethylamino-benzaldehyde were boiled under reflux in 50 ml of ethanol overnight. After evaporation of the solvent the residue was again taken up in 20 ml of ethanol, 0.05 g of sodium borohydride was added thereto and the mixture was left to react at room temperature overnight. The excess sodium borohydride was then decomposed by the addition of 5 ml of glacial acetic acid and the solvent was evaporated. After the addition of 10 ml of methanol the mixture was again evaporated. Addition of methanol and evaporation were repeated again, whereafter the mixture was purified by chromatography on 30 g of silica gel with a mixture of dichloromethane and methanol in the ratio by volume 10:1. The product-containing fractions were combined and evaporated, and the residue was taken up in 5 ml of ethanol. After the addition of 5 ml of 3N isopropanolic hydrochloric acid the hydrochloride of the product precipitated and was recrystallized from ethanol/diethyl ether.

Workup

  1. customAfter evaporation of the solvent the residue
  2. addition0.05 g of sodium borohydride was added
  3. waitthe mixture was left
  4. customto react at room temperature overnight
  5. customthe solvent was evaporated
  6. additionAfter the addition of 10 ml of methanol the mixture
  7. customwas again evaporated
  8. additionAddition of methanol and evaporation
  9. customwas purified by chromatography on 30 g of silica gel with a mixture of dichloromethane and methanol in the ratio by volume 10:1
  10. customevaporated
  11. additionAfter the addition of 5 ml of 3N isopropanolic hydrochloric acid the hydrochloride of the product
  12. customprecipitated
  13. customwas recrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-fcf9fda80e4a48cf8a66bc455659b111
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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