Hydrochloric Acid → HCID 18771026, compound

HRID 479449Notes

Reaction equation

HRID 479449 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:8][C:9]3([O:21][C:5]=2[CH:4]=1)[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]CC)=[O:17])[CH2:11][CH2:10]3.[OH-].[Li+].[ClH:32]>C(O)C>[ClH:32].[C:16]([CH2:15][N:12]1[CH2:13][CH2:14][C:9]2([CH:8]=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:6]3[CH:28]=[CH:29][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[O:21]2)[CH2:10][CH2:11]1)([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18770960HCID 18770960, compound

Product 1

HCID 18771026HCID 18771026, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

A mixture of ethyl 7-methoxy-4-phenylspiro[2H-1-benzopyran-2,4′-piperidine]-1′-acetate (3.38 g, 8.60 mmol), ethyl alcohol (250 cm3) and aqueous lithium hydroxide solution (2 N, 6.44 cm3, 12.88 mmol) was heated to reflux for 3.5 h. Upon cooling, the mixture was treated with hydrochloric acid (5 N, 70 cm3) and some of the ethyl alcohol was removed until precipitation began. The mixture was then cooled to 4° C. until crystallisation was complete. The solid was removed by vacuum filtration to afford the title product as a white solid, m.p. 195-230° C., positive ion ESI (M+H)+366.4.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3.5 h
  3. temperatureUpon cooling
  4. customsome of the ethyl alcohol was removed until precipitation
  5. customThe solid was removed by vacuum filtration

Sources & evidence

ORD record
ord-e322397b329c494aa705d523cb19e3c0
Source dataset
uspto-grants-2003_11
Patent number
US06645973B1

Reaction notes

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