Formaldehyde → (S)-4-Benzyl-1-methyl-2-(2-methylsulfanyl-ethyl)-piperazine

HRID 131389Notes

Reaction equation

HRID 131389 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][CH2:15][S:16][CH3:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:20](O[BH-](OC(=O)C)OC(=O)C)(=[O:22])C.[Na+].[OH-].[Na+]>C(Cl)Cl>[NH3:8].[CH3:20][OH:22].[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH3:20])[C@@H:10]([CH2:14][CH2:15][S:16][CH3:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 17750451(S)-1-Benzyl-3-(2-(methylthio)ethyl)piperazine

Product 2

HCID 21705897Ammonia methanolHCID 58626059(S)-4-Benzyl-1-methyl-2-(2-methylsulfanyl-ethyl)-piperazineYield 190.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine (S)-1-benzyl-3-(2-methylsulfanyl-ethyl)-piperazine (0.900 g, 3.59 mmol) and 37% formaldehyde solution (0.4 mL, 5.39 mmol) in methylene chloride (15 mL). Stir for 10 minutes and add sodium triacetoxy borohydride (3.05 g, 14.4 mmol). Stir an additional 90 minutes and then pour solution onto 1N sodium hydroxide solution. Extract with methylene chloride to give 0.947 g of the crude product. Silica gel chromatography, eluting with methylene chloride:2N ammonia/methanol (100:2), gives 0.906 g of the title compound as a colorless oil; mass spectrum (ion spray): m/z =265 (M+1).

Workup

  1. stirringStir an additional 90 minutes
  2. extractionExtract with methylene chloride
  3. customto give 0.947 g of the crude product
  4. washSilica gel chromatography, eluting with methylene chloride

Sources & evidence

ORD record
ord-28ea5dfaccea4b2da373912865ec1f95
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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