3,4-Dichlorophenol → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3,4-dichlorophenoxy)piperidine hydrochloride

HRID 1462069ノート

反応式

HRID 1462069 の反応式
[F:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]3)=[N:7][O:8][C:4]=2[CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24](O)[CH:25]=[CH:26][C:27]=1[Cl:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1>[ClH:21].[F:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH:15]([O:18][C:25]4[CH:24]=[CH:23][C:22]([Cl:21])=[C:27]([Cl:28])[CH:26]=4)[CH2:16][CH2:17]3)=[N:7][O:8][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 72583,4-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 133198661-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxypiperidine

生成物 1

HCID 133198631-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3,4-dichlorophenoxy)piperidine hydrochloride

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

To a solution of 6.4 g of 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxypiperidine, 3.7 g of 3,4-dichlorophenol and 6.6 g of triphenylphosphine in 200 ml of benzene, cooled with an ice bath, was slowly added over one hr a solution of 4.4 g of diethyl azodicarboxylate in 50 ml of benzene. After stirring twenty hrs at ambient temperature, the reaction mixture was filtered and the filtrate was concentrated. The residue was treated with ethereal hydrogen chloride to yield a salt. The salt was rebasified to given an oil, which was purified by column chromatography (silica gel, tetrahydrofuran). The purified oil was treated with ethereal hydrogen chloride, and the resultant salt was recrystallized from ethyl acetate/methanol to give 2.4 g (23%) or product, mp 212°-214° C.

後処理

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was treated with ethereal hydrogen chloride
  4. customto yield a salt
  5. customwas purified by column chromatography (silica gel, tetrahydrofuran)
  6. additionThe purified oil was treated with ethereal hydrogen chloride
  7. customthe resultant salt was recrystallized from ethyl acetate/methanol
  8. customto give 2.4 g (23%) or product, mp 212°-214° C.

出典と根拠

ORDレコード
ord-f5204afcd74846719cb9106e72157c2d
出典データセット
uspto-grants-1984_07
特許番号
US04458075

反応ノート

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