Methane → N-(1-ADAMANTYL)-3-OXO-BUTANAMIDE

HRID 426547Notes

Reaction equation

HRID 426547 reaction equation
[NH2:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:12]=[C:13]1[O:17][C:15](=[O:16])[CH2:14]1.C>C1C=CC=CC=1>[C:2]12([NH:1][C:15](=[O:16])[CH2:14][C:13](=[O:17])[CH3:12])[CH2:3][CH:4]3[CH2:10][CH:8]([CH2:7][CH:6]([CH2:5]3)[CH2:11]1)[CH2:9]2

Participants

5

Reactant 3

HCID 297MethaneHCID 2130AmantadineHCID 12661Diketene

Product 1

HCID 360023N-(1-ADAMANTYL)-3-OXO-BUTANAMIDE

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

19 g of 1-amino-adamantane were added to 200 ml of benzene and then 9.5 ml of diketene were added thereto over 10 minutes. The mixture was stirred for 21/2 hours at room temperature and after the addition of activated charcoal, the mixture was stirred and filtered. The filtrate was distilled to dryness under reduced pressure and the residue was added to isopropyl ether. The mixture was vacuum filtered to obtain 23.6 g of N-(1-adamantyl)-acetylacetamide melting at 80° C. 23.5 g of the said product and 1 g of p-toluene sulfonic acid were added to a mixture of 50 ml of methanol and 15 ml of methyl orthoformate and the mixture was stirred at room temperature for 24 hours and was then cooled. 2 ml of quinoline were added and the mixture was vacuum filtered. The precipitate was dried to obtain 25.1 g of N-(1-adamantyl)-3,3-dimethoxy-butyramide melting at 140° C.

Workup

  1. stirringthe mixture was stirred
  2. filtrationfiltered
  3. distillationThe filtrate was distilled to dryness under reduced pressure
  4. additionthe residue was added to isopropyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c671e25fdff440deaee275221568c154
Source dataset
uspto-grants-1979_10
Patent number
US04170465

Reaction notes

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