Hydrochloric Acid → HCID 21310617, compound

HRID 583131Notes

Reaction equation

HRID 583131 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][C:16](=[O:18])[N:15]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:14]=2)[C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:12]=1.Cl[CH2:26][CH2:27][CH2:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([N:37]([CH3:39])[CH3:38])[CH2:33][CH2:32]1)=[O:30].C(N(CC)CC)C.Cl>C(#N)C.C(O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][C:16](=[O:18])[N:15]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][C:29]([N:31]4[CH2:32][CH2:33][CH:34]([N:37]([CH3:39])[CH3:38])[CH2:35][CH2:36]4)=[O:30])[CH2:21][CH2:20]3)[N:14]=2)[C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 21310621HCID 21310621, compoundHCID 23212658HCID 23212658, compound

Product 1

HCID 21310617HCID 21310617, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

1 g (2.68 mmol) of 5-(6-chloro-3,4-dihydro-2H-benzopyran-8-yl)-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one hydrochloride, in solution in 50 ml of acetonitrile, is introduced into a 250 ml three-necked round-bottomed flask, 1.24 ml (5.36 mmol) of 1-(4-chloro-1-oxobutyl)-N,N-dimethylpiperidin-4-amine and 1.12 ml (8 mmol) of triethylamine are added and the mixture is stirred at room temperature overnight. The mixture is evaporated under reduced pressure and the residue is taken up in water and extracted three times with chloroform. The organic phase is dried over magnesium sulphate and filtered, the solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, elution being carried out with 98/2, 95/5 and then 90/10 mixtures of dichloromethane and methanol. A white solid is obtained which is treated in a solution of gaseous hydrochloric acid in ethanol and, after recrystallizing from ethanol, 0.22 g of hydrochloride is finally isolated. Melting point: 193° C.

Workup

  1. customThe mixture is evaporated under reduced pressure
  2. extractionextracted three times with chloroform
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent is evaporated under reduced pressure
  6. customthe residue is purified by chromatography on a column of silica gel, elution
  7. customA white solid is obtained which
  8. customafter recrystallizing from ethanol, 0.22 g of hydrochloride
  9. customis finally isolated

Sources & evidence

ORD record
ord-ee9ab08b07fc4e54a1c477f637d62b59
Source dataset
uspto-grants-1999_07
Patent number
US05929089

Reaction notes

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