3-Chloro-N,N-dimethyl-1-propanamine → HCID 68129596, compound

HRID 917873Notes

Reaction equation

HRID 917873 reaction equation
[Na].[CH2:2]([O:4][C:5]([C:7]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([O:20][CH3:21])[CH:14]=2)[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:10]([CH3:27])[NH:9][C:8]=1[CH3:28])=[O:6])[CH3:3].[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33]Cl>C(O)C>[CH2:2]([O:4][C:5]([C:7]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:33][CH2:32][CH2:31][N:30]([CH3:35])[CH3:29])=[C:15]([O:20][CH3:21])[CH:14]=2)[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:10]([CH3:27])[NH:9][C:8]=1[CH3:28])=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 6198691,4-Dihydro-4-(4-hydroxy-3-methoxyphenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl esterHCID 5360545Sodium

Product 1

HCID 68129596HCID 68129596, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.3 g of sodium in 100 ml of ethanol is added to a warm solution of 37.5 g of 2,6-dimethyl-4-(3-methoxy-4-hydroxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester (melting point 172°C) in 300 ml of ethanol. The mixture is heated at reflux and 15 g of 3-dimethylaminopropyl chloride are added dropwise. After refluxing for several hours, the mixture is filtered hot, the residue being washed with alcohol, and the filtrate is evaporated in vacuo to yield yellow crystals of melting point 62°C after recrystallization from ligroin-petroleum ether.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. temperatureAfter refluxing for several hours
  4. filtrationthe mixture is filtered hot
  5. washthe residue being washed with alcohol
  6. customthe filtrate is evaporated in vacuo
  7. customto yield yellow crystals of melting point 62°C
  8. customafter recrystallization from ligroin-petroleum ether

Sources & evidence

ORD record
ord-e1e2fff214ef414c85b3ae8ce63f558b
Source dataset
uspto-grants-1976_07
Patent number
US03968117

Reaction notes

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