1,2-Dichloroethane → [3-(Benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-methyl-amine

HRID 2220358Notes

Reaction equation

HRID 2220358 reaction equation
ClC(OC(Cl)=O)C.[S:8]1[CH:12]=[CH:11][C:10]2[C:13]([O:17][CH:18]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:19][CH2:20][N:21](CC3C=CC=CC=3)[CH3:22])=[CH:14][CH:15]=[CH:16][C:9]1=2.ClCCCl.N>CO>[S:8]1[CH:12]=[CH:11][C:10]2[C:13]([O:17][CH:18]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:19][CH2:20][NH:21][CH3:22])=[CH:14][CH:15]=[CH:16][C:9]1=2

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 5213051-Chloroethyl chloroformateHCID 10316919[3-(Benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-benzyl-methyl-amine

Product 1

HCID 10221261[3-(Benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-methyl-amineYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Add 1-chloroethylchloroformate (0.58 mL, 5.38 mmol) to a stirred solution of [3-(benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-benzyl-methyl-amine (0.9619 g, 2.62 mmol) and 1,2-dichloroethane (25 mL). Heat the reaction to reflux under nitrogen for 1.5 hours. Add methanol (30 mL) and heat the reaction at reflux for 30 minutes. Cool the reaction to room temperature and make it basic using 2M ammonia in methanol. Concentrate on a rotary evaporator to give the crude product. Purify the crude product by flash chromatography on silica gel eluting with 0.5% concentrated ammonium hydroxide/5% ethanol/chloroform to yield 0.6303 g (87%) of [3-(benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-methyl-amine: mass spectrum (ion spray) m/z=278.2(M+1); HPLC (90/5/5 to 0/95/5 water/acetonitrile/5% formic acid in water) XTerra MS C18 2.1 mm×50 mm×3.5 micron: Retention time: 2.52 minutes, Purity: >99.9%.

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux under nitrogen for 1.5 hours
  4. customthe reaction
  5. temperatureat reflux for 30 minutes
  6. temperatureCool
  7. customthe reaction to room temperature
  8. concentrationConcentrate on a rotary evaporator
  9. customto give the crude product
  10. customPurify the crude product by flash chromatography on silica gel eluting with 0.5% concentrated ammonium hydroxide/5% ethanol/chloroform

Sources & evidence

ORD record
ord-66332f795ba8495c8620326b0b74374b
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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