1-Chloroethyl chloroformate → HCID 89602350, compound

HRID 2175740Notes

Reaction equation

HRID 2175740 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:20]C(OC(Cl)C)=O>ClCCl.O.CO>[ClH:20].[S:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[CH2:14][C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1

Participants

6

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 89610023HCID 89610023, compound

Product 1

HCID 89602350HCID 89602350, compoundYield 94.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of 1-benzyl-4-(thiophen-2-ylmethyl)-1,2,3,6-tetra hydropyridine (1) (3.3 g, 12.26 mmol) in dichloromethane (30 mL) was added 1-chloroethyl chloroformate (12.27 g, 85.87 mmol) at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 3 h. Then the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated to get residue; which was dissolved in methanol (20 mL) and heated at 70-80° C. for 1 h. The reaction mixture was rotary evaporated under vacuum to get residue which was triturated with diethyl ether to get the desired compound as a brown solid (2.5 g); 1H NMR (400 MHz, DMSO-d6) δ 9.04-8.92 (m, 2H), 7.38 (dd, J=1.5, 5.4 Hz, 1H), 6.97 (dd, J=3.4, 5.4 Hz, 1H), 6.90 (dd, J=1.0, 3.4 Hz, 1H), 5.54 (s, 1H), 3.56 (s, 2H), 3.54-3.52 (m, 2H), 3.14-3.11 (m, 2H), 2.24-2.16 (m, 2H).

Workup

  1. extractionextracted with dichloromethane (50 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was rotary evaporated
  6. customto get residue
  7. temperatureheated at 70-80° C. for 1 h
  8. customThe reaction mixture was rotary evaporated under vacuum
  9. customto get residue which
  10. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-05543a56ce0f49c5b1990e7069fac3ff
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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