1-Chloroethyl chloroformate → HCID 67783210, compound

HRID 129081Notes

Reaction equation

HRID 129081 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:15]1[CH2:20][CH2:19][CH2:18][C:17](=[CH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[CH2:16]1)C1C=CC=CC=1>C(Cl)Cl>[ClH:1].[C:28]([C:25]1[CH:24]=[CH:23][C:22]([CH:21]=[C:17]2[CH2:18][CH2:19][CH2:20][NH:15][CH2:16]2)=[CH:27][CH:26]=1)#[N:29]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 53806431HCID 53806431, compound

Product 1

HCID 67783210HCID 67783210, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.8 g of 1-chloroethyl chloroformate in 5 ml of methylene chloride are added dropwise to 2.9 g of 1-benzyl-3-(4-cyanobenzylidene)piperidine in 20 ml of methylene chloride at 0° C. and the mixture is stirred at 0° C. for 30 minutes. After 20 minutes at ambient temperature, it is evaporated down, the residue is taken up in 20 ml of methanol and the mixture is reflux-heated for 30 minutes. The reaction solution is evaporated down, and the residue is triturated with 100 ml of ethyl acetate and suction-filtered. 1.9 g of 3-(4-cyanobenzylidene)piperidine hydrochloride are obtained as a colourless powder.

Workup

  1. waitAfter 20 minutes at ambient temperature
  2. customit is evaporated down
  3. temperaturethe mixture is reflux-heated for 30 minutes
  4. customThe reaction solution is evaporated down
  5. customthe residue is triturated with 100 ml of ethyl acetate
  6. filtrationsuction-filtered

Sources & evidence

ORD record
ord-28eed88fa1c548fa9b3ce634acfe479f
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Reaction notes

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