Hydrochloric Acid → HCID 86734379, compound

HRID 1414555Notes

Reaction equation

HRID 1414555 reaction equation
C(O)(=O)C(O)=O.[CH2:7]([N:10]1[CH2:15][CH2:14][C:13]2([C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([O:29]C)[C:23]=3[O:22][C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:11]1)[C:8]#[CH:9].[ClH:31].N1C=CC=CC=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O.N1C=CC=CC=1>[Cl:31][CH:9]=[CH:8][CH2:7][N:10]1[CH2:15][CH2:14][C:13]2([C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([OH:29])[C:23]=3[O:22][C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 86734380HCID 86734380, compound

Product 1

HCID 86734379HCID 86734379, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1'-(prop-2-ynyl)-4-methoxyxanthene-9-spiro-4'-piperidine hydrogen oxalate (1.3 g.) and pyridine hydrochloride prepared from pyridine (9 ml.) and concentrated hydrochloric acid (10 ml.) is heated at 200° C. for 10 minutes. The mixture is cooled and water (20 ml.) added. The solution is basified with dilute sodium carbonate solution and extracted with ether. The ether extract is washed with water, dried with MgSO4 and evaporated to dryness. The solid residue is recrystallised from ethyl acetate-petroleum ether (b.p. 80°-100° C.) to give 1'-(3-chloro-prop-2-enyl)-4-hydroxyxanthene-9-spiro-4'-piperidine, m.p. 153°-155° C.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried with MgSO4
  6. customevaporated to dryness
  7. customThe solid residue is recrystallised from ethyl acetate-petroleum ether (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-ab9d5ec427c84a3a85b346b923731769
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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