Benzaldehyde → HCID 67925318, compound

HRID 1087810Notes

Reaction equation

HRID 1087810 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH2:11])[CH3:10])=[CH:4][CH:3]=1.[CH:12](=O)[C:13]1C=CC=C[CH:14]=1.S(OC)(O[CH3:24])(=O)=O.[ClH:27].C(=O)([O-])[O-].[K+].[K+].C(Br)C#C>C1(C)C=CC=CC=1.O.C1C=CC=CC=1>[ClH:27].[CH3:24][N:11]([CH:9]([CH3:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:12]#[C:13][CH3:14]

Participants

10

Reactant 6

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 7842Propargyl bromideHCID 99864-FluoroamphetamineHCID 11430Potassium Carbonate

Product 1

HCID 67925318HCID 67925318, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To 7.65 g. (0.05 mole) of (±)-2-(4-fluoro-phenyl)-1-methyl-ethyl-amine (BE-PS 609 630) in 25 ml. of benzene 5.3 g. (0.05 mole) of distilled benzaldehyde are added and the solution is allowed to stand overnight and dried. To the dried solution 6.3 g. (0.05 mole) of dimethyl sulphate are added and the mixture is allowed to boil under reflux for 3 hours and after cooling under stirring a solution of 2 ml. conc. hydrochlorid acid in 50 ml. of water is added. After stirring for 1 hour the two layers are separated and the aqueous - acidic layer is alkalized with sodium hydroxide and extracted with benzene. The benzene solution is dried and evaporated and the residue is distilled in vacuo. The main cut (4.15 g., bp.: 87°-90° C./10 mmHg) is dissolved in 40 ml. of toluene and after adding 23.5 g. (0.17 mole) of potassium carbonate a solution of 3.65 g. (0.031 mole) propargyl bromide in 60% toluene is added dropwise to the mixture and it is stirred for 14 hours at room temperature. The mixture is then filtered and the filtrate acidified with 31% ethanol containing HCl until pH=3. The crystalline product is filtered and recrystallized from a mixture of ethanol and ether. 2.1 g. of (±)-N-methyl-N-propynyl-2-(4-fluoro-phenyl)-1-methyl-1-ethyl-amine hydrochloride are obtained, m.p.: 130°-132° C.

Workup

  1. customdried
  2. temperatureunder reflux for 3 hours
  3. temperatureafter cooling
  4. stirringAfter stirring for 1 hour the two layers
  5. customare separated
  6. extractionextracted with benzene
  7. dry with materialThe benzene solution is dried
  8. customevaporated
  9. distillationthe residue is distilled in vacuo
  10. dissolutionThe main cut (4.15 g., bp.: 87°-90° C./10 mmHg) is dissolved in 40 ml
  11. additionof toluene and after adding 23.5 g
  12. stirringis stirred for 14 hours at room temperature
  13. filtrationThe mixture is then filtered
  14. additioncontaining HCl until pH=3
  15. filtrationThe crystalline product is filtered
  16. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-0aad488c25574b23bfd507d145439bfc
Source dataset
uspto-grants-1990_10
Patent number
US04960797

Reaction notes

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