Ammonia → HCID 13608116, compound

HRID 435984Notes

Reaction equation

HRID 435984 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.Cl.[CH2:16]=[O:17].N>S(=O)(=O)(O)O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH2:16][OH:17])[CH2:12][N:11]([CH3:14])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 155325Pyridine, 4-(4-fluorophenyl)-1,2,3,6-tetrahydro-1-methyl-

Product 1

HCID 13608116HCID 13608116, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

4-(4-Fluorophenyl)-1-methyl-1,2,3,6-tetrahydropyridine (50 g) was dissolved in a mixture of 21.6 ml of concentrated sulphuric acid and 50 ml of water. To the solution were added 25 ml of concentrated hydrochloric acid and 22.4 ml of 37% formaldehyde solution. The mixture was refluxed for 5 hours, cooled, and 125 ml of concentrated ammonia were added. The mixture was extracted with 50 ml of toluene. Drying of the toluene solution and distillation gave 38 g of 4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,6-tetrahydropyridine with b.p. 110°-120° C at 0.1 mm Hg.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with 50 ml of toluene
  4. dry with materialDrying of the toluene solution and distillation

Sources & evidence

ORD record
ord-a771aee8b8d24df480938a41ea16d100
Source dataset
uspto-grants-1977_02
Patent number
US04007196

Reaction notes

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