1-Chloroethyl chloroformate → (2,6-Dichloro-phenyl)-(4-morpholin-2-yl-phenyl)-amine

HRID 588242Notes

Reaction equation

HRID 588242 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])=[CH:16][CH:15]=2)[CH2:9]1)C1C=CC=CC=1.CC(Cl)OC(Cl)=O>ClCCCl>[Cl:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([Cl:27])[C:21]=1[NH:20][C:17]1[CH:16]=[CH:15][C:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 66653766[4-(4-Benzyl-morpholin-2-yl)-phenyl]-(2,6-dichloro-phenyl)-amine

Product 1

HCID 66654215(2,6-Dichloro-phenyl)-(4-morpholin-2-yl-phenyl)-amineYield 60.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dichloro-phenyl)-amine (0.72 g; 1.74 mmol) in 1,2-dichloroethane (5 mL) was added, drop wise, ACE-Cl (0.40 mL; 3.66 mmol) at 0° C. The resulting mixture was stirred at room temperature, overnight, and subsequently concentrated in vacuo. To the residue was added toluene and the mixture was concentrated in vacuo. This last step was repeated twice. To the final residue was added MeOH (5 mL), and this mixture was stirred overnight at RT. Once more the mixture was concentrated in vacuo. The residue was partitioned between EtOAc and 2 M Aqueous NaOH. The layers were separated, and the organic layer dried (Na2SO4), filtered, and concentrated in vacuo to afford (2,6-dichloro-phenyl)-(4-morpholin-2-yl-phenyl)-amine (0.34 g); which was used as such.

Workup

  1. customat 0° C
  2. concentrationsubsequently concentrated in vacuo
  3. additionTo the residue was added toluene
  4. concentrationthe mixture was concentrated in vacuo
  5. additionTo the final residue was added MeOH (5 mL)
  6. stirringthis mixture was stirred overnight at RT
  7. concentrationOnce more the mixture was concentrated in vacuo
  8. customThe residue was partitioned between EtOAc and 2 M Aqueous NaOH
  9. customThe layers were separated
  10. dry with materialthe organic layer dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c71054398c8a400c8ff91d625164c402
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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