Ethanol → 2-[2-[4-[Bis(4-fluorophenyl)methyl]-1-piperidinyl]ethyl]2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione oxalate hydrate

HRID 247324Notes

Reaction equation

HRID 247324 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5]1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:20][CH:19]=1.[C:38]([O-:41])([O-:40])=O.[K+].[K+].C([OH:46])C>>[OH2:5].[C:6]([OH:5])(=[O:46])[C:38]([OH:41])=[O:40].[F:37][C:34]1[CH:35]=[CH:36][C:31]([CH:24]([C:21]2[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=2)[CH:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH:4]3[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]4[CH:13]=[CH:14][CH:15]=[N:16][C:6]=4[O:5]3)[CH2:27][CH2:26]2)=[CH:32][CH:33]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 137264422-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)thione

Product 1

HCID 137293342-[2-[4-[Bis(4-fluorophenyl)methyl]-1-piperidinyl]ethyl]2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione oxalate hydrate

Procedure

A solution of 4 g (0.016 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione and 4.5 g (0.016 mole) of 4-[bis(4-fluorophenyl)-methyl]piperidine in 100 ml of ethanol was refluxed for 48 hr. One gram of K2CO3 was added and this mixture stirred at reflux for 144 hr. The mixture was concentrated and the residue partitioned between chloroform and dilute sodium hydroxide. The chloroform was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a Waters® 500 HPLC using a silica column and eluting with absolute ethanol. The material with mass 507 was collected and concentrated. The residue (6 g) was reacted with 1.2 g of oxalic acid in ethanol. Yield was 5 g, m.p. 125°-138° C.

Workup

  1. temperatureat reflux for 144 hr
  2. concentrationThe mixture was concentrated
  3. customthe residue partitioned between chloroform and dilute sodium hydroxide
  4. dry with materialThe chloroform was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a Waters® 500 HPLC
  7. washeluting with absolute ethanol
  8. customThe material with mass 507 was collected
  9. concentrationconcentrated
  10. customThe residue (6 g) was reacted with 1.2 g of oxalic acid in ethanol

Sources & evidence

ORD record
ord-03eb88a9618e483a9bf37738bcb6dec2
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

Loading…