Triethylamine → N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine

HRID 1064405

反応式

HRID 1064405 の反応式
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.[Cl:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[C:22](Cl)[C:21]([CH3:28])=[C:20]([CH3:29])[N:19]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:10]([N:7]1[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][NH:1][C:22]2[C:21]([CH3:28])=[C:20]([CH3:29])[N:19]=[C:18]([Cl:17])[C:23]=2[N+:24]([O-:26])=[O:25])[CH2:9][CH2:8]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 18670022-(1-Benzylpiperidin-4-yl)ethan-1-amineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

生成物 1

HCID 21973806N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine収率 60.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 4-(2-aminoethyl)-1-benzylpiperidine (9.88 g, 45.2 mmol) in N,N-dimethylformamide was added dropwise to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (10.00 g, 45.2 mmol) and triethylamine (12.6 mL, 90.5 mmol) in N,N-dimethylformamide (320 mL). The reaction mixture was allowed to stir at ambient temperature for about 20 hours and then it was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organics were combined, washed with brine, dried over sodium sulfate and then concentrated under reduced pressure to provide an orange oil. The oil was purified by flash chromatography (400 mL silica gel eluting initially with 10% ethyl acetate in hexane, then with 15% ethyl acetate in hexane and finally with 40% ethyl acetate in hexane) to provide 11.00 g of N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine.

後処理

  1. concentrationit was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto provide an orange oil
  9. customThe oil was purified by flash chromatography (400 mL silica gel eluting initially with 10% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-b832268912f548858064938c6b6ad439
出典データセット
uspto-grants-2005_11
特許番号
US06969722B2

関連ノート

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