Hydrochloric Acid → N-(5-fluoro-2-methylphenyl)-3-(hydroxymethyl)-1-piperazineacetamide

HRID 35335ノート

反応式

HRID 35335 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([NH:8][C:9](=[O:22])[CH2:10][N:11]2[CH2:16][CH2:15][N:14]3C(C)(C)[O:18][CH2:19][CH:13]3[CH2:12]2)[CH:7]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([NH:8][C:9](=[O:22])[CH2:10][N:11]2[CH2:16][CH2:15][NH:14][CH:13]([CH2:19][OH:18])[CH2:12]2)[CH:7]=1

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 21295689N-(5-fluoro-2-methylphenyl)-tetrahydro-3,3-dimethyl-3H-oxazolo[3,4-a]pyrazine-7(8H)-acetamide

生成物 1

HCID 14230238N-(5-fluoro-2-methylphenyl)-3-(hydroxymethyl)-1-piperazineacetamide収率 59.4%

実験手順

A mixture of 8.5 parts of N-(5-fluoro-2-methylphenyl)tetrahydro-3,3-dimethyl-3H-oxazolo[3,4-a]pyrazine-7(8H)-acetamide and 105.6 parts of hydrochloric acid solution 0.5N was stirred and refluxed for 2 hours. The reaction mixture was cooled to room temperature. The whole was alkalized with sodium carbonate and salted out. The product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia (85:15 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was triturated in 2,2'-oxybispropane. The product was filtered off and dried, yielding 4.4 parts (59.4%) of N-(5-fluoro-2-methylphenyl)-3-(hydroxymethyl)-1-piperazineacetamide; mp. 127.7° C. (intermediate 145).

後処理

  1. temperaturerefluxed for 2 hours
  2. extractionThe product was extracted with trichloromethane
  3. washThe extract was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was triturated in 2,2'-oxybispropane
  12. filtrationThe product was filtered off
  13. customdried

出典と根拠

ORDレコード
ord-16b3cb96e1244c6b9f4458937914dcfc
出典データセット
uspto-grants-1988_08
特許番号
US04766125

反応ノート

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