Ammonium Acetate → 1-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]-4-phenylpiperidin-4-ol

HRID 1192558노트

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HRID 1192558 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][C:18]([OH:27])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:34].[Na+]>CO.C(#N)C>[NH2:34][CH:12]([C:10]1[C:9]([N:15]2[CH2:20][CH2:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([OH:27])[CH2:17][CH2:16]2)=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([Cl:1])[CH:11]=1)[CH3:13]

참가 물질

6

반응물 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368555HCID 58368555, 화합물

생성물 1

HCID 583685331-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]-4-phenylpiperidin-4-ol

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

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온도
65 °C

실험 절차

A mixture of 1-[5-chloro-8-(4-hydroxy-4-phenylpiperidin-1-yl) quinolin-7-yl]ethanone (37 mg, 0.097 mmol) and ammonium acetate (74.9 mg, 0.971 mmol) in methanol (0.55 mL) and acetonitrile (0.55 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (12.2 mg, 0.194 mmol). The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate, extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness (35 mg, 94%). LCMS calculated for C22H25ClN3O (M+H)+: m/z=382.2; Found: 382.1.

후처리

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. for another 4 hours
  3. temperaturecooled to room temperature
  4. customquenched with sat. sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness (35 mg, 94%)

출처 및 근거

ORD 기록
ord-1c2cc74f5b8849cbbd9debfe38efce87
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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