1-Chloroethyl chloroformate → HCID 69981714, compound

HRID 1837187Notes

Reaction equation

HRID 1837187 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])[O:11][CH3:12])C.[Cl:21]C(OC(Cl)C)=O>ClC(Cl)C>[ClH:21].[CH3:12][O:11][C:6]1([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[CH2:4][NH:2][CH3:1]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 23497857HCID 23497857, compound

Product 1

HCID 69981714HCID 69981714, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a magnetically stirred solution of (+/−)-3-(2-dimethylaminomethyl-1-methoxy-cyclohexyl)-benzonitrile (0.10 g, 0.367 mmol) in anhydrous dichloroethane (2 mL) at room temperature under Ar atmosphere was added 1-chloroethyl chloroformate (0.059 mL, 0.825 mmol). After stirring at 100° C. for 2 hours, the reaction was concentrated in vacuo to a crude solid. MeOH (5 mL) was added and the reaction mixture was stirred at 90° C. for 2 hours. The reaction mixture was concentrated in vacuo to a crude oil. The pure amine was obtained by column chromatography over silica gel (0.5:100 TEA/EtOAc as eluent) which gave the free base (0.10 g, 94%). 1H NMR (CDCl3) 1.64-2.09 (m, 11H), 2.17 (s, 3H), 2.33 (m, 1H), 3.16 (s, 3H), 7.47 (d, J=7.6 Hz, 1H), 7.55 (m, 2H), 7.61 (m, 1H). 13C NMR (75 MHz, CDCl3) 21.6, 25.9, 26.6, 32.4, 36.7, 48.3, 50.3, 52.9, 80.7, 112.4, 119.2, 129.1, 130.3, 130.4, 131.1, 145.9.

Workup

  1. concentrationthe reaction was concentrated in vacuo to a crude solid
  2. additionMeOH (5 mL) was added
  3. stirringthe reaction mixture was stirred at 90° C. for 2 hours
  4. concentrationThe reaction mixture was concentrated in vacuo to a crude oil

Sources & evidence

ORD record
ord-64049dfeb16f4496a3270255d71f6bdb
Source dataset
uspto-grants-2004_08
Patent number
US06780891B2

Reaction notes

Loading…