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

HRID 1192558ノート

反応式

HRID 1192558 の反応式
[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]

参加物

6

反応物 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368555HCID 58368555、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-1c2cc74f5b8849cbbd9debfe38efce87
出典データセット
uspto-grants-2014_03
特許番号
US08680108B2

反応ノート

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