Hydrochloric Acid → HCID 131717885, compound

HRID 1781354Notes

Reaction equation

HRID 1781354 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:26][CH2:25][C:15]3([S:20][C:19]4[S:21][CH:22]=[CH:23][C:18]=4[C:17](=[O:24])[CH2:16]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-])=[O:2].[OH-].[Na+].C(=O)(O)[O-].[Na+].[ClH:34]>C(O)(=O)C.O>[OH2:2].[ClH:34].[ClH:34].[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][C:15]3([S:20][C:19]4[S:21][CH:22]=[CH:23][C:18]=4[C:17](=[O:24])[CH2:16]3)[CH2:25][CH2:26]2)=[CH:6][CH:5]=1.[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][C:15]3([S:20][C:19]4[S:21][CH:22]=[CH:23][C:18]=4[C:17](=[O:24])[CH2:16]3)[CH2:25][CH2:26]2)=[CH:6][CH:5]=1.[ClH:34].[ClH:34]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 67724782HCID 67724782, compound

Product 1

HCID 131717885HCID 131717885, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution Of 1.1 g (2.8 mmoles) of 1-(2-(p-nitrophenyl)ethyl)spiro(piperidine-4,6'-(6H)-thieno-[2,3-b]thiopyran)-4'(5'H)-one in 15 mL acetic acid and 20 mL H2O was treated with 15 mL of a solution of 15% TiCl3 in 20% HCl. The dark purple reaction mixture was stirred at room temperature for 45 minutes and poured into 200 mL water. The pH was adjusted to 9 with 2 N NaOH and saturated sodium bicarbonate. The aqueous mixture was extracted several times with ethyl acetate. The combined organics were dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 955 mg. A small amount was treated with excess ethanolic HCl and the hydrochloride was crystallized from ethanol to give 55 mg of product, m.p. 240° C.

Workup

  1. extractionThe aqueous mixture was extracted several times with ethyl acetate
  2. dry with materialThe combined organics were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give 955 mg
  6. customthe hydrochloride was crystallized from ethanol

Sources & evidence

ORD record
ord-ed27f126b77d43e6a1c1da3462a9297f
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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