Phosgene → HCID 59863032, compound

HRID 2064066Notes

Reaction equation

HRID 2064066 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.[C:23](Cl)(Cl)=[O:24].C(N(CC)CC)C>ClCCl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:23](=[O:24])[N:9]([CH:10]3[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]3)[C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 57423910HCID 57423910, compound

Product 1

HCID 59863032HCID 59863032, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,1-Dimethylethyl 4-[(2-amino-5-chlorophenyl)amino]-1-piperidinecarboxylate (D28) (5.8 g) was dissolved in 100 ml of dichloromethane at 0° C. and phosgene (20% in toluene, 10 ml) and triethylamine (5.6 ml) were added and the mixture was stirred at 0° C. for 1 h, then washed with aqueous citric acid, dried over MgSO4, filtered and evaporated The product was crystallised from diethyl ether to yield the title compound, 5.7 g.

Workup

  1. washwashed with aqueous citric acid
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated The product
  5. customwas crystallised from diethyl ether

Sources & evidence

ORD record
ord-78cc5d8a778a4467839a0aed8a6e065e
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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