p-Toluenesulfonic acid → 4-(1-Benzylpiperidin-4-yl)morpholine

HRID 642909

反応式

HRID 642909 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(O)(=O)C>[C:2]1([CH2:1][N:8]2[CH2:13][CH2:12][CH:11]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 5

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 51700761-Benzyl-2-piperidone

生成物 1

HCID 7838314-(1-Benzylpiperidin-4-yl)morpholine

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

30 mL (0.162 Mol) 1-benzylpiperidone (L) and 16.1 mL (0.185 Mol) morpholine (M) are dissolved in 407 mL tetrahydrofuran at ambient temperature. While cooling, 1.0 g (5 mmol) of p-toluenesulphonic acid and 14.6 mL glacial acetic acid are added, whereupon a jelly-like precipitate is formed. 52.19 g (0.246 Mol) sodium triacetoxyborohydride are added while cooling with ice, during which time the reaction temperature rises to 30° C. After 4 hours at 20° C., 90 mL water are added dropwise. After another 30 minutes, 280 mL of 17% potassium carbonate solution are added. The mixture is stirred intensively, while gas is observed to be given off. After separation of the phases the organic phase is dried and evaporated down. Yield: 33.0 g (78% of theory)

後処理

  1. temperatureWhile cooling
  2. customis formed
  3. temperaturewhile cooling with ice, during which time the reaction temperature
  4. customrises to 30° C
  5. waitAfter another 30 minutes
  6. customAfter separation of the phases the organic phase
  7. customis dried
  8. customevaporated down

出典と根拠

ORDレコード
ord-b152b6f43a19429a8b1b02915dbfe146
出典データセット
uspto-grants-2010_04
特許番号
US07696346B2

関連ノート

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