Hydrochloric Acid → HCID 19772049, compound

HRID 1614636Notes

Reaction equation

HRID 1614636 reaction equation
O.[ClH:2].[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1.[Cl:25][CH2:26][CH2:27][N:28]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][C:29]1=[O:39].C(=O)(O)[O-].[Na+].[I-].[K+].Cl>C(O)CCC>[ClH:25].[ClH:2].[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:26][CH2:27][N:28]3[C:37](=[O:38])[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:39])[CH2:14][CH2:13]2)=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 787663-(2-chloroethyl)(1H,3H)quinazoline-2,4-dioneHCID 516892Sodium BicarbonateHCID 19771956HCID 19771956, compound

Product 1

HCID 19772049HCID 19772049, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2.89 g (7.52 mmol) of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine hydrochloride hydrate, 1.74 g (7.75 mmol) of 3-(2-chloroethyl)-2,4(1H,3H)quinazolinedione, 7.56 g (90 mmol) of sodium bicarbonate, and 0.20 g (1.20 mmol) of potassium iodide in 250 mL of 1-butanol was heated at reflux for 20 h. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The organic phase was dried (Na2SO4), and the solvent was removed in vacuo. The residue was subjected to flash chromatography (silica gel, eluted with 1-3% CH3OH in CH2Cl2) to give the free base of the product. This was converted to the HCl salt, and the salt was recrystallized from CH3OH/diethyl ether to give 1.80 g (42.7%) of the title compound as a white solid, mp 213°-220° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between CH2Cl2 and dilute NaOH
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customthe solvent was removed in vacuo
  7. washThe residue was subjected to flash chromatography (silica gel, eluted with 1-3% CH3OH in CH2Cl2)
  8. customto give the free base of the product
  9. customthe salt was recrystallized from CH3OH/diethyl ether

Sources & evidence

ORD record
ord-ce4c2d5a19544d0cb39aa02c72af95bc
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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