Formic Acid → HCID 131710804, compound

HRID 2399126Notes

Reaction equation

HRID 2399126 reaction equation
C(O)=O.[C:4]1([CH:10]2[CH:17]3[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:19][C:11]2([CH2:20][CH:21]([CH3:24])[NH:22][CH3:23])[CH2:12]4)[CH2:16]3)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:25]=O.[ClH:27]>CCOCC.O>[ClH:27].[C:4]1([CH:10]2[CH:17]3[CH2:16][CH:15]4[CH2:14][CH:13]([CH2:12][C:11]2([CH2:20][CH:21]([CH3:24])[N:22]([CH3:25])[CH3:23])[CH2:19]4)[CH2:18]3)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 35974N-Methyl-1-(2-phenyladamantan-1-yl)propan-2-amine

Product 1

HCID 131710804HCID 131710804, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Formic acid (4.5 ml.) and water (0.5 ml.) were added to the 2-phenyl-N,α-dimethyl-1-adamantaneethylamine (1.0 g.) followed by a 40 percent formaldehyde solution (5 ml.). The mixture was heated on a boiling water bath for seven hours and then allowed to stand overnight. The aqueous solvents were removed in vacuo and the residue treated with dilute hydrochloric acid. Excess acid was removed in vacuo and the oily residue extracted between 3N sodium hydroxide and ether. The organic phase was washed twice with water and dried over magnesium sulfate. The ether was then removed in vacuo to leave 1.1 g. of the base as an oil. The base was dissolved in dry ether, and ethereal hydrochloric acid was added in excess. The resulting precipitate was filtered off and dried in vacuo, and then crystallized from an ethanol-ether mixture to yield 0.3 g. of crystals. Recrystallization from an ethanol-ether mixture yielded 2-phenyl-N,N,α-trimethyl-1-adamantaneethylamine hydrochloride, m.p., 186° -90° C.

Workup

  1. temperatureThe mixture was heated on a boiling water bath for seven hours
  2. customThe aqueous solvents were removed in vacuo
  3. additionthe residue treated with dilute hydrochloric acid
  4. customExcess acid was removed in vacuo
  5. extractionthe oily residue extracted between 3N sodium hydroxide and ether
  6. washThe organic phase was washed twice with water
  7. dry with materialdried over magnesium sulfate
  8. customThe ether was then removed in vacuo
  9. customto leave 1.1 g
  10. filtrationThe resulting precipitate was filtered off
  11. customdried in vacuo
  12. customcrystallized from an ethanol-ether mixture
  13. customto yield 0.3 g
  14. customRecrystallization from an ethanol-ether mixture

Sources & evidence

ORD record
ord-4dfbb09e2b7e47699456746ea66c2c42
Source dataset
uspto-grants-1977_05
Patent number
US04027035

Reaction notes

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