Dimethylamine → HCID 13787827, compound

HRID 1380442Notes

Reaction equation

HRID 1380442 reaction equation
C=O.CNC.[S:6](=[O:10])(=[O:9])([OH:8])[OH:7].S(O)(O)(=O)=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:24]2([CH2:31][CH2:32][CH3:33])[CH:29]=[CH:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[CH:21]=[CH:22][CH:23]=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([C:42]2([CH2:49][CH2:50][CH3:51])[CH:47]=[CH:46][N:45]([CH3:48])[CH2:44][CH2:43]2)[CH:39]=[CH:40][CH:41]=1.[OH-].[Na+]>O.CCCCCC>[S:6]([OH:10])([OH:9])(=[O:8])=[O:7].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:24]2([CH2:31][CH2:32][CH3:33])[CH:25]=[CH:26][N:27]([CH3:30])[CH2:28][CH2:29]2)[CH:21]=[CH:22][CH:23]=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([C:42]2([CH2:49][CH2:50][CH3:51])[CH2:43][CH2:44][N:45]([CH3:48])[CH:46]=[C:47]2[CH2:26][N:27]([CH3:30])[CH3:28])[CH:39]=[CH:40][CH:41]=1

Participants

10

Reactant 6

HCID 674Dimethylamine2×HCID 712FormaldehydeHCID 1118Sulfuric Acid3×HCID 14798Sodium HydroxideHCID 13671256HCID 13671256, compoundHCID 70357437HCID 70357437, compound

Product 2

HCID 13787827HCID 13787827, compoundHCID 70357437HCID 70357437, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 10 g (0.123 mol) of 37% aqueous formaldehyde and 15 g (0.133 mol) of 40% aqueous dimethylamine in 100 ml of water was added enough concentrated sulfuric acid so as to adjust the pH of the reaction mixture to 3-4. A solution of 25 g (0.0867 mol) of 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine sulfate in approximately 40 ml of water was added and the pH adjusted to 3-3.5, if necessary, by the addition of sulfuric acid or 40% aqueous dimethylamine. The 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine sulfate solution was prepared by the extraction of 25 g of 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine in 50 ml of hexane with a total of about 40 ml of 2.5N sulfuric acid. The mixture was stirred at approximately 65°-70° C. for 2 hours while maintaining the pH of the reaction mixture between 3-3.5. The solution was cooled to 30° C. and added to 100 ml of 25% sodium hydroxide. The resulting suspension was extracted twice with 50 ml portions of hexane. The organic extracts were combined and washed five times with 50 ml portions of water, one time with a 50 ml portion of saturated sodium chloride and dried over 5 g of anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure afforded 28.4 g of crude 1,4,5,6-tetrahydro-4-(3-methoxyphenyl)-N,N,1-trimethyl-4-propyl-3-pyridinemethanamine as an oil. Purity 85% by NMR.

Workup

  1. temperaturewhile maintaining the pH of the reaction mixture between 3-3.5
  2. extractionThe resulting suspension was extracted twice with 50 ml portions of hexane
  3. washwashed five times with 50 ml portions of water, one time with a 50 ml portion of saturated sodium chloride
  4. dry with materialdried over 5 g of anhydrous sodium sulfate
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b8aca887e2e9487d80cb6e36eaf64c71
Source dataset
uspto-grants-1986_04
Patent number
US04581456

Reaction notes

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