Water → HCID 20216103, compound

HRID 236551Notes

Reaction equation

HRID 236551 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[OH:16])[C:5]([N:7]1[CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[OH:16])[CH2:5][N:7]1[CH2:8][CH:9]=[CH:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20216117HCID 20216117, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20216103HCID 20216103, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 1-(3-chloro-4-hydroxybenzoyl)-1,2,3,6-tetrahydropyridine (13.6 g.) in hot, dry tetrahydrofuran (300 ml.) was added slowly to a stirred suspension of lithium aluminium hydride (5.44 g.) in dry tetrahydrofuran (100 ml.). The mixture was heated under reflux for 17 hours and then cooled. Water (5.5 ml.), 15% w/v aqueous sodium hydroxide solution (5.5 ml.) and water (15 ml.) were added successively and the mixture was stirred for 1 hour and then filtered. The filtrate was evaporated and water (100 ml.) added to the residue. The mixture was filtered and the filtrate was acidified to pH2 with concentrated hydrochloric acid, and cooled to 5° C. The crystalline precipitate which formed was separated, washed with water (20 ml.), then with acetone (20 ml.), and recrystallised from methanol-acetone to give 1-(3-chloro-4-hydroxybenzyl)-1,2,3,6-tetrahydropyridine hydrochloride (6.6 g.), m.p. 225°-231° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 17 hours
  3. temperaturecooled
  4. additionwere added successively
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. additionwater (100 ml.) added to the residue
  8. filtrationThe mixture was filtered
  9. customThe crystalline precipitate which formed
  10. customwas separated
  11. washwashed with water (20 ml.)
  12. customwith acetone (20 ml.), and recrystallised from methanol-acetone

Sources & evidence

ORD record
ord-54459da7b3a1472b88e5c43f69b8cc2a
Source dataset
uspto-grants-1987_02
Patent number
US04645771

Reaction notes

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