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Hydrochloric Acid → N-{1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-piperidyl}-4-fluorobenzamide hydrochloride

HRID 1493873
ノート
印刷プレビュー

反応式

HRID 1493873 の反応式
Br[CH2:2][CH2:3][CH:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1.[ClH:14].[NH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>CC(=O)CC.CC(C)=O.C(O)(C)C>[ClH:14].[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:4]([CH2:3][CH2:2][N:15]2[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:19][CH2:20]2)[CH2:5][CH2:6]1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 143302824-(2-bromoethyl)-3,4-dihydro-2H-benzopyranHCID 198294144-Fluoro-N-(piperidine-4-yl)benzamide hydrochloride

生成物 1

HCID 19829444N-{1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-piperidyl}-4-fluorobenzamide hydrochloride
収率 63.3%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 3776Isopropanol溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

The procedure is as in Example 4, but starting with 4-(2-bromoethyl)-3,4-dihydro-2H-benzopyran (1.9 g), N-(4-piperidyl)-4-fluorobenzamide hydrochloride (2 g), dry potassium carbonate (2.15 g) and potassium iodide (0.95 g) in 2-butanone (60 cc). The yellow oil obtained is purified by chromatography on a column 4 cm in diameter containing a silica gel (110 g), eluting with a toluene/diethylamine/ethanol mixture (60:20:20 by volume) (300 cc) and collecting 30-cc fractions. The fractions between 330 and 900 cc are concentrated to dryness. The yellow crystals obtained are dissolved in acetone (25 cc) and treated with a 3.4N solution (3 cc) of hydrochloric acid in isopropanol. The precipitate formed is filtered off on sintered glass and then recrystallized in an ethanol/acetone mixture (20:60 by volume) (80 cc). After the addition of ethyl ether (10 cc), N-{1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-piperidyl}-4-fluorobenzamide hydrochloride (2.05 g) is obtained in the form of a crystalline white solid, m.p. 240° C.

後処理

  1. customThe yellow oil obtained
  2. customis purified by chromatography on a column 4 cm in diameter
  3. additioncontaining a silica gel (110 g)
  4. washeluting with a toluene/diethylamine/ethanol mixture (60:20:20 by volume) (300 cc)
  5. customcollecting 30-cc fractions
  6. concentrationThe fractions between 330 and 900 cc are concentrated to dryness
  7. customThe yellow crystals obtained
  8. customThe precipitate formed
  9. filtrationis filtered off on sintered glass
  10. customrecrystallized in an ethanol/acetone mixture (20:60 by volume) (80 cc)
  11. additionAfter the addition of ethyl ether (10 cc)

出典と根拠

ORDレコード
ord-b6992bca6f8247e4894f784274d32a19
出典データセット
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05025013

反応ノート

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