Triphosgene → HCID 178451871, compound

HRID 1058620Notes

Reaction equation

HRID 1058620 reaction equation
[NH2:1][C:2]1[C:3]([Cl:28])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl.C(=O)([O-])O.[Na+]>ClCCCl.C(N(CC)CC)C>[Cl:28][C:3]1[C:2]2[N:1]=[C:30]([OH:32])[N:12]([CH2:13][CH2:14][CH:15]3[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:19][CH2:20]3)[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1

Participants

6

Reactant 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 18668783HCID 18668783, compound

Product 1

HCID 178451871HCID 178451871, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 0.60 g of tert-butyl 4-[2-(3-amino-2-chloro-4-quinolylamino)-ethyl]-1-piperidinecarboxylate and 0.44 g of triphosgene in 10 ml of 1,2-dichloroethane, 0.41 ml of triethylamine was added dropwise, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution, and extracted with 1,2-dichloroethane. The extract was washed with saturated brine, and dried, and the solvent was evaporated. The residue was washed with diisopropyl ether to give 0.57 g of colorless crystals. Recrystallization from 1,2-dichloroethane gave colorless crystals having the melting point of from 222 to 223° C.

Workup

  1. extractionextracted with 1,2-dichloroethane
  2. washThe extract was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated
  5. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-8816a9787e3a46399bd142428b87447e
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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