1-Chloroethyl chloroformate → Hydrochloric Acid

HRID 1361519Notes

Reaction equation

HRID 1361519 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])([C:14]#[N:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:24]C(OC(Cl)=O)C>C(Cl)Cl>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:11]1([C:14]#[N:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1.[ClH:24]

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 49760213HCID 49760213, compound

Product 2

HCID 313Hydrochloric AcidHCID 231499534-(2-Methoxyphenyl)piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-4-(2-methoxy-phenyl)-piperidine-4-carbonitrile 7a (6.17 g, 0.02 mol) in CH2Cl2 (200 mL) was added dropwise chloroformic acid 1-chloroethyl ester (3.66 g, 0.03 mol). After stirred for 5 h the mixture was concentrated under reduced pressure and methanol (200 mL) was added. The mixture was then heated to reflux for 30 min. The solvent was removed under vacuum. Diethyl ether (100 mL) was added and the white precipitate was collected by filtration to afford 4-(2-methoxyphenyl)piperidine-4-carbonitrile 7b as HCl salt. 1H NMR (CDCl3) δ 9.5-9.1 (br, 2H), 7.41 (t, J=7.6 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 7.02 (t, J=7.6 Hz, 1H), 3.87 (s, 3H). 3.44 (d, J=13.2 Hz, 2H), 3.08 (m, 2H), 2.48 (m, 2H), 2.28 (m, 2H). MS (ESI) m/z (M+H+) 217.2.

Workup

  1. concentrationwas concentrated under reduced pressure and methanol (200 mL)
  2. additionwas added
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for 30 min
  5. customThe solvent was removed under vacuum
  6. additionDiethyl ether (100 mL) was added
  7. filtrationthe white precipitate was collected by filtration

Sources & evidence

ORD record
ord-8b735e15a4ce44e89080587b887f80e0
Source dataset
uspto-grants-2011_02
Patent number
US07880007B2

Reaction notes

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