Calcium Carbonate → N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 84075노트

반응식

HRID 84075 반응식
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[Ca+2].[I:26]Cl>CO>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([I:26])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

참가 물질

5

반응물 3

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 22292800HCID 22292800, 화합물

생성물 1

HCID 22292785N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine수율 71.4%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1.50 g, 5.22 mmol) in methanol (70 mL) was treated with CaCO3 (1.06 g, 10.44 mmol) followed by a solution of ICl (1.70 g, 10.44 mmol) in methanol (10 mL), and stirred overnight at 20 C. The product mixture was filtered, concentrated, dissolved in EtOAc (200 mL), extracted twice with 5% aqueous sodium bisulfite (100 mL), once with brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 1.54 g of a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.55 (m, 1H), 6.57 (m, 1H), 3.86 (s, 3H), 3.80 (m, 1H), 3.60-3.30 (m, 2H), 3.20-2.80 (m, 4H), 1.30 (m, 3H). MS calculated for C14H15F3INO2+H: 414, observed: 414.

후처리

  1. filtrationThe product mixture was filtered
  2. concentrationconcentrated
  3. dissolutiondissolved in EtOAc (200 mL)
  4. extractionextracted twice with 5% aqueous sodium bisulfite (100 mL), once with brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-edee2e43641343f99449a46873e8afdd
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846906B2

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