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Tetrahydrofuran → HCID 54413708, compound

HRID 1464147
Notes
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Reaction equation

HRID 1464147 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:13][CH2:12][CH2:11][CH2:10][S:9]2)=[CH:4][CH:3]=1.O1CCCC1.C([Li])CCC.[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([CH2:29][CH2:30][N:31]([CH2:33][CH:34]([CH3:37])[CH2:35]Cl)[CH3:32])=[CH:27][CH:26]=1>CCCCCC.O>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH:34]([CH3:37])[CH2:35][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[S:9][CH2:10][CH2:11][CH2:12][S:13]2)=[CH:38][CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 251992-(4-Chlorophenyl)-1,3-dithianeHCID 20079712HCID 20079712, compoundHCID 178418339Butyllithium

Product 1

HCID 54413708HCID 54413708, compound

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 8058HexaneSolvent

Procedure

2.77 g (0.012 mol) of 2-(4-chlorophenyl)-m-dithiane and 10 ml of abs. tetrahydrofuran were cooled to -70° in a sulphonation flask while gassing with argon and treated with 7.50 ml (0.012 mol) of butyllithium in hexane. Thereupon, the mixture was stirred at -20° for 2 hours. A solution of 2.50 g (0.0096 mol) of rac-4-chloro-N-(3-chloro-2-methylpropyl)-N-methylphenethylamine in abs. tetrahydrofuran was added dropwise thereto at -70° within 15 minutes, whereupon the mixture was left to stand at -20° for 18 hours and at room temperature for 3 hours. The reaction solution was then poured into water and extracted three times with ether. The ethereal extracts were dried over magnesium sulphate and evaporated. The residual oil was chromatographed on silica gel with toluene-hexane (1:1). After evaporating the solvent and warming the residue at 50° for 18 hours under reduced pressure there was obtained rac-N-(4-chlorophenethyl)-2-(4-chlorophenyl)-β,N-dimethyl-m-dithiane-2-propanamine as a viscous oil.

Workup

  1. waitat -70° within 15 minutes
  2. waitwhereupon the mixture was left
  3. waitto stand at -20° for 18 hours and at room temperature for 3 hours
  4. extractionextracted three times with ether
  5. dry with materialThe ethereal extracts were dried over magnesium sulphate
  6. customevaporated
  7. customThe residual oil was chromatographed on silica gel with toluene-hexane (1:1)
  8. customAfter evaporating the solvent
  9. temperaturewarming the residue at 50° for 18 hours under reduced pressure

Sources & evidence

ORD record
ord-a178c7ab8e2547478af6345d63da1306
Source dataset
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05302727

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes