Dimethylamine, hydrochloride → HCID 22609607, compound

HRID 2306783Notes

Reaction equation

HRID 2306783 reaction equation
[OH-].[K+].Cl.[CH3:4][NH:5][CH3:6].[C:7]1([CH3:34])[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:22][C:21](=O)[CH2:20][N:19]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[C:7]1([CH3:34])[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:22][CH:21]([N:5]([CH3:6])[CH3:4])[CH2:20][N:19]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2×HCID 15507463HCID 15507463, compound

Product 1

HCID 22609607HCID 22609607, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Addition of 102 mg (1.8 mmol) of potassium hydroxide to a solution of 479 mg (5.9 mmol) of dimethylamine hydrochloride in methanol (4 ml) gave a clear solution. To this solution were added 979 mg (2.3 mmol) of 1,4-bis(p-toluenesulfonyl)-6-oxohexahydro-1,4-diazepine synthesized by the above process in methanol (30 ml) and 116 mg (1.8 mmol) of sodium cyanoborohydride. After the resultant mixture was stirred for 15 hours at room temperature, 104 mg (1.7 mmol) of additional sodium cyanoborohydride was added, and the mixture was stirred for an additional 25 hours. A 1N aqueous solution (5 ml) of sodium hydroxide was added to the reaction mixture, and the mixture was concentrated under reduced pressure, followed by extraction with chloroform. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel to obtain 519 mg (yield: 50%) of 1,4-bis(p-toluenesulfonyl)-6-(N,N-dimethylamino)-hexahydro-1,4-diazepine as a colorless oil.

Workup

  1. customgave a clear solution
  2. concentrationthe mixture was concentrated under reduced pressure
  3. extractionfollowed by extraction with chloroform
  4. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d1a9372d307d42cf8be21e704d59b08d
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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