Triethylamine → HCID 18668740, compound

HRID 1058616Notes

Reaction equation

HRID 1058616 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[NH2:23][CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH2:27]1.C(OCC)(=O)C>CN(C)C=O.O>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:23][CH2:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:28][CH2:27]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27851382,4-Dichloro-3-nitroquinolineHCID 18668763HCID 18668763, compound

Product 1

HCID 18668740HCID 18668740, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 22.6 g of 2,4-dichloro-3-nitroquinoline and 13.0 ml of triethylamine in 60 ml of N,N-dimethylformamide, a solution of 23.0 g of 4-(2-aminoethyl)-N-triphenylmethylpiperidine in 40 ml of N,N-dimethylformamide was added dropwise with stirring under ice-cooling. The mixture was stirred at room temperature for 1 hour. The reaction mixture was added with ethyl acetate and water. The precipitated crystals were collected by filtration, and washed successively with ethyl acetate and diethyl ether to give 26.9 g of yellow crystals. Recrystallization from a mixture of N,N-dimethylformamide and ethyl acetate gave yellow crystals having the melting point of from 223.5 to 231° C. (decomposition).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed successively with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-1c091ec53b4d41028cb21b30d9ae1454
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

Loading…