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

HRID 280894노트

반응식

HRID 280894 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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 give 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.

후처리

  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. customto give an oil, which
  6. customwas purified by column chromatography (silica gel, tetrahydrofuran)
  7. additionThe purified oil was treated with ethereal hydrogen chloride
  8. customthe resultant salt was recrystallized from ethyl acetate/methanol
  9. customto give 2.4 g (23%) or product, mp 212°-214° C.

출처 및 근거

ORD 기록
ord-3482b72fd7dd455984afc6575b2610f9
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04591586

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