Formaldehyde → HCID 21436304, compound

HRID 1283986Notes

Reaction equation

HRID 1283986 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][CH:9]2[C:14](=[C:15]([CH3:17])[CH3:16])[CH2:13][CH2:12][CH2:11][NH:10]2)=[CH:6][CH:5]=1.C=O.[CH2:22](N(CC)CC)C.[H][H]>C(O)C>[CH3:22][N:10]1[CH2:11][CH2:12][CH2:13][C:14](=[C:15]([CH3:17])[CH3:16])[CH:9]1[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 21436291HCID 21436291, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21436304HCID 21436304, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.8 g. 2-(p-methoxybenzyl)-3-isopropylidenepiperidine hydrochloride, 0.8 ml. of 35% aqueous formaldehyde solution, 1.4 ml. of triethylamine, and ethanol to a total volume of 50 ml. was shaken at room temperature under 50 p.s.i. of hydrogen. The theoretical quantity of hydrogen was consumed in 1 hour. The reaction mixture was filtered and the residue thus collected was rinsed with a small amount of ethanol. Th filtrate and rinse were combined and evaporated to dryness under reduced pressure and the residue was partitioned between dilute ammonium hydroxide and diethyl ether. The ether layer was washed with water, dried, and filtered, and the filtrate evaporated to dryness under reduced pressure to give 1.9 g of 1-methyl-2-(p-methoxybenzyl)-3-isopropylidenepiperidine as a syrup. This was taken up in 50 ml. of diethyl ether and treated with a slight excess of ethereal hydrogen chloride to precipitate a gum. Addition of 5 ml. of isopropyl alcohol and trituration caused crystallization. Recrystallization from 5 ml. of isopropyl alcohol and 50 ml. of diethyl ether afforded the pure compound which melted at 179°-183°C; ir (KBr) 1670 cm-1 (tetrasubstituted double bond); nmr (of base, CDCl3): 147 (s,3); 93 (s,3); 63 (d3, J=1-2 cps).

Workup

  1. additionA mixture of 2.8 g
  2. customThe theoretical quantity of hydrogen was consumed in 1 hour
  3. filtrationThe reaction mixture was filtered
  4. customthe residue thus collected
  5. washwas rinsed with a small amount of ethanol
  6. washTh filtrate and rinse
  7. customevaporated to dryness under reduced pressure
  8. customthe residue was partitioned between dilute ammonium hydroxide and diethyl ether
  9. washThe ether layer was washed with water
  10. customdried
  11. filtrationfiltered
  12. customthe filtrate evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-16a79913351143cdb77c71c9160a2aaa
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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