Tetrahydrofuran → Phenylmethyl 4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate

HRID 1457611ノート

反応式

HRID 1457611 の反応式
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C.C1COCC1>O>[CH2:1]([O:8][C:9]([N:12]1[CH2:13][CH2:14][CH:15]([CH2:18][NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:17]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 16004294N-(Phenylmethyl)-4-piperidinemethanamine

生成物 1

HCID 22099453Phenylmethyl 4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate収率 50%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Under ice-cooling, 3.46 g of benzyloxycarbonyl chloride was added dropwise to a mixed solution of 4.15 g of N-(4-piperidylmethyl)-N-benzylamine, 2.10 g of triethylamine and 200 ml of THF. After stirring the mixture at the same temperature for 3 hours and then at room temperature for 2 hours, water was added to the mixture and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; chloroform:methanol=19:1) to give 3.41 g of N-(1-benzyloxycarbonylpiperidin-4-ylmethyl)-N-benzylamine (yield: 50%, IR: 1702 cm-1).

後処理

  1. temperatureUnder ice-cooling
  2. waitat room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (solvent; chloroform:methanol=19:1)

出典と根拠

ORDレコード
ord-ef52abcfdcbe4472953f7438bd2c445b
出典データセット
uspto-grants-1998_12
特許番号
US05849732

反応ノート

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