2-Chloroethyl chloroformate → HCID 22100972, compound

HRID 1457807Notes

Reaction equation

HRID 1457807 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH2:11][CH2:12][N:13](CC2C=CC=CC=2)[CH2:14][CH:15]=1.[Cl:23]C(OCCCl)=O>ClCCl>[ClH:23].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=1

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 9861313HCID 9861313, compound

Product 1

HCID 22100972HCID 22100972, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(benzothiophen-2-yl)-1-benzyl-1,2,3,6-tetrahydropyridine (3.5 g, 0.01 mol) in anhydrous dichloromethane (50 ml) cooled in ice was added chloroethyl chloroformate (1.61 ml, 0.013 mol). The reaction was stirred at room temperature for 11/2 hours and concentrated in vacuo. The residue was suspended in methanol (25 ml) and stirred under reflux for 1 hour. The reaction mixture was cooled, and the resultant solid isolated by filtration, to afford the title compound as a pale yellow solid (2.1 g, 84%). δH (DMSO-d6), 2.80 (2H, m, HNCH2CH2), 3.34 (2H, m, HNCH2CH2), 3.77 (2H, m, HNCH2CH2), 6.21 (1H, m, HNCH2CH), 7.35 (2H, m, ArH), 7.49 (1H, s, ArH), 7.81 (1H, m, ArH), 7.92 (1H, m, ArH).

Workup

  1. concentrationconcentrated in vacuo
  2. stirringstirred
  3. temperatureunder reflux for 1 hour
  4. temperatureThe reaction mixture was cooled
  5. customthe resultant solid isolated by filtration

Sources & evidence

ORD record
ord-1bb2378eb9884b35b9489a570c3de5d7
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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