Toluene → HCID 19030882, compound

HRID 1708277Notes

Reaction equation

HRID 1708277 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:37]=[CH:36][C:16]([C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][CH2:28][C:26]3=[O:27])[CH2:21][CH2:20]2)=[O:18])=[CH:15][CH:14]=1.[O:38]([C:40]#[N:41])[Na].C1(C)C=CC=CC=1>C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:40]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([N:19]2[CH2:20][CH2:21][CH:22]([N:25]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][CH2:28][C:26]3=[O:27])[CH2:23][CH2:24]2)=[O:18])=[CH:36][CH:37]=1)(=[O:38])[NH2:41]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 19030918HCID 19030918, compoundHCID 178418852HCID 178418852, compound

Product 1

HCID 19030882HCID 19030882, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid (0.21 ml) is added dropwise with stirring to a mixture of 1-{1-[4-(3-hydroxypropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.51 g), NaOCN (0.16 g), toluene (5 ml) and chloroform (5 ml) at room temperature. After adding, the mixture is stirred at room temperature overnight. Ethyl acetate is added to the reaction mixture and the mixture is washed with saturated aqueous sodium hydrogen carbonate solution, water and saline solution successively and then dried with sodium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1) to give 1-{1-[4-(3-carbamoyloxypropoxy)benzoyl-4-piperidinyl}-3,4-dihydrocarbostyril (0.15 g).

Workup

  1. additionAfter adding
  2. washthe mixture is washed with saturated aqueous sodium hydrogen carbonate solution, water and saline solution successively
  3. dry with materialdried with sodium sulfate
  4. distillationThe solvent is distilled off
  5. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1)

Sources & evidence

ORD record
ord-350f79e6d2c1475bbbe456b903fc82d9
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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