Hydrochloric Acid → HCID 23373708, compound

HRID 865935Notes

Reaction equation

HRID 865935 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:19]=[C:20]([CH:29]=[CH:30][CH:31]=2)[C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=O)[CH2:13][CH2:12]1)[CH3:3].C1(C)C=CC=CC=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:48]2)=CC=1.[OH-].[Na+].[ClH:63]>>[ClH:63].[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:19]=[C:20]([CH:29]=[CH:30][CH:31]=2)[C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[S:48])[CH2:13][CH2:12]1)[CH3:3]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 14798Sodium HydroxideHCID 60820MazapertineHCID 87949Lawesson's reagent

Product 1

HCID 23373708HCID 23373708, compound

Conditions

Temperature
90 °C

Procedure

A solution of 1-[3-[[4-[2-(1-methylethoxy)phenyl]-1-piperazinyl]methyl]benzoyl]piperidine (CP #36, 3.86 g, 0.0092 mol) and toluene (50 mL) was treated with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (2.22 g, 0.0055 mole) and the resulting mixture was heated at 90° C. for 1 h. The reaction was cooled followed by the addition of toluene (50 mL), and mixed thoroughly with excess 3N sodium hydroxide solution. The organic layer was separated, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated to an oily residue. Chromatography of this material on flash silica, using 1.5-2.5% methanol in methylene chloride, afforded CP #1 which was converted to its hydrochloride salt in ethereal hydrochloric acid, 3.61 g (77%), m.p. 221°-224° C. (dec, uncorrected). The structural assignment was supported by 1H NMR, chemical-ionization MS, and IR data.

Workup

  1. temperatureThe reaction was cooled
  2. customThe organic layer was separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to an oily residue
  6. customafforded CP #1 which

Sources & evidence

ORD record
ord-c4ef0384909445058f2a58f98d104018
Source dataset
uspto-grants-1996_10
Patent number
US05569659

Reaction notes

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