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Hydrochloric Acid → (2R)-2-[2-(3,4-dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol

HRID 227545
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인쇄 미리보기

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HRID 227545 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH2:15][CH2:16][OH:17])[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31].Cl>C1(C)C=CC=CC=1.O.C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH2:15][CH2:16][OH:17])[O:14][CH2:13][CH2:12][N:11]([C:30](=[O:31])[C:29]3[CH:28]=[C:27]([O:26][CH3:25])[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 10956756(2R)-2-[2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol

생성물 1

HCID 12042117(2R)-2-[2-(3,4-dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol수율 104.5%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 1140Toluene용매2회
HCID 6342Acetonitrile용매

반응 조건

온도
2.5 °C

실험 절차

To a mixture of (2R)-2-[2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol (25 g, 90.3 mmol) and acetonitrile (125 ml), triethylamine (27.4 g, 271 mmol) was added under a nitrogen stream, the resulting mixture was cooled to 0-5° C., then a solution of 3,4,5-trimethoxybenzoyl chloride (21.24 g, 92.1 mmol) in toluene (100 ml) was further added dropwise at below 10° C., and then the mixture was stirred at 0-5° C. for one hour. After completion of the reaction, toluene (150 ml), water (125 ml) and concentrated hydrochloric acid (25 ml) were added to the reaction mixture, and the resulting mixture was partitioned. The separated organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and water, and concentrated to afford (2R)-2-[2-(3,4-dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol (44.4 g) as an oil.

후처리

  1. additionwas added under a nitrogen stream
  2. additionwere added to the reaction mixture
  3. customthe resulting mixture was partitioned
  4. washThe separated organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and water
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d14ec9bb909849c6aea7a07340e91c86
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560549B2

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