N,N-Diphenylcarbamic chloride → HCID 20502518, compound

HRID 851120Notes

Reaction equation

HRID 851120 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][N:12]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15](=[O:16])[C:13]2=[O:14])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[C:35]1([N:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:42](Cl)=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[C:35]1([N:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:42]([N:6]2[CH2:7][CH2:8][N:3]([CH2:9][CH2:10][CH2:11][N:12]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:15](=[O:16])[C:13]3=[O:14])[CH2:4][CH2:5]2)=[O:43])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 65741N,N-Diphenylcarbamic chlorideHCID 11708267BistrimethylsilylacetamidHCID 20502541HCID 20502541, compound

Product 1

HCID 20502518HCID 20502518, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-[3-(1-piperazinyl)propyl]isatin dihydrochloride (1.39 g) in methylene chloride (40 ml) was added bis(trimethylsilyl)acetamide (3.44 g), and the mixture was stirred for 10 minutes. After N,N-diphenylcarbamoyl chloride (1.16 g) was added thereto, the stirring was continued at the ambient temperature for 5 hours. The reaction mixture was poured into ice-water and the methylene chloride layer was separated, washed with water and then dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was crystallized from diethyl ether to obtain N,N-diphenyl-4-[3-(isatin-1-yl)propyl]piperazine-1-carboxamide (0.62 g), mp. 163° to 164.5° C.

Workup

  1. waitthe stirring was continued at the ambient temperature for 5 hours
  2. customthe methylene chloride layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-feccfaebe02e486d82d2b1ddef22d292
Source dataset
uspto-grants-1983_05
Patent number
US04382934

Reaction notes

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