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Triethylamine → N-[1-[3-(4-fluorophenoxy)propyl]-4-methyl-4-piperidinyl]acetamide

HRID 2294209
ノート
印刷プレビュー

反応式

HRID 2294209 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.Cl.[CH3:14][C:15]1([NH:21][C:22](=[O:24])[CH3:23])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C>[I-].[K+].CN(C)C=O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:18]2[CH2:19][CH2:20][C:15]([NH:21][C:22](=[O:24])[CH3:23])([CH3:14])[CH2:16][CH2:17]2)=[CH:7][CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 743911-(3-Chloropropoxy)-4-fluorobenzeneHCID 21472474N-(4-methylpiperidin-4-yl)acetamide hydrochloride

生成物 1

HCID 21472471N-[1-[3-(4-fluorophenoxy)propyl]-4-methyl-4-piperidinyl]acetamide収率 39.6%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
70 °C

実験手順

A mixture of 35.84 g of 1-(3-chloropropoxy)-4-fluorobenzene, 33 g of N-(4-methyl-4-piperidinyl)acetamide monohydrochloride, 54 ml of N,N-diethylethanamine, 0.1 g of potassium iodide and 1000 ml of N,N-dimethylformamide was stirred and heated for 1.5 hours at 70° C. The reaction mixture was cooled and the solvent was evaporated. The residue was taken up in a sodium carbonate solution in water and the product was extracted with dichloromethane. The extract was washed successively twice with water, twice with a sodium carbonate solution in water and again with water, dried, filtered and evaporated. The residue was purified by column chromatography (CHCl3 :CH3OH 95:5 by volume). The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried in vacuo at 50° C., yielding 20.93 g of N-[1-[3-(4-fluorophenoxy)propyl]-4-methyl-4-piperidinyl]acetamide; mp. 103.4° C. (interm. 2).

後処理

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was evaporated
  3. extractionthe product was extracted with dichloromethane
  4. washThe extract was washed successively twice with water, twice with a sodium carbonate solution in water and again with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (CHCl3 :CH3OH 95:5 by volume)
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 2,2'-oxybispropane
  12. filtrationThe product was filtered off
  13. customdried in vacuo at 50° C.

出典と根拠

ORDレコード
ord-30d6f0f2bb424482baa43945e28a7f5a
出典データセット
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05688814

反応ノート

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