Hydrochloric Acid → HCID 86734383, compound

HRID 2286902Notes

Reaction equation

HRID 2286902 reaction equation
[ClH:1].C([O:5][C:6]1[C:11]2[O:12][C:13]3[C:18]([C:19]4([CH2:24][CH2:23][N:22]([CH2:25][C:26]#[CH:27])[CH2:21][CH2:20]4)[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)(=O)C.Cl.C(=O)(O)[O-].[Na+]>CCOCC>[ClH:1].[OH:5][C:6]1[C:11]2[O:12][C:13]3[C:18]([C:19]4([CH2:24][CH2:23][N:22]([CH2:25][C:26]#[CH:27])[CH2:21][CH2:20]4)[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 86734385HCID 86734385, compound

Product 1

HCID 86734383HCID 86734383, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Acetoxy-1'-(prop-2-ynyl)xanthene-9-spiro-4'-piperidine hydrochloride (0.4 g.) is stirred with 3 N hydrochloric acid (20 ml.) at room temperature for 24 hours. The solution is basified using solid sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate extract is dried over MgSO4 and evaporated to give a gummy residue which is dissolved in ether and treated with ethereal hydrochloric acid. The precipitate is recrystallised from ethanol-ether to give 4-hydroxy-1'-(prop-2-ynyl)xanthene-9-spiro-4'-piperidine hydrochloride, m.p. 246°-247° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. dry with materialis dried over MgSO4
  4. customevaporated
  5. customto give a gummy residue which
  6. customThe precipitate is recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-77620ec1017e4c3fadf482ff8235ad88
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

Loading…