N,N-Dimethylethylenediamine → Benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylate

HRID 516406ノート

反応式

HRID 516406 の反応式
Cl[S:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25]>C1COCC1>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH:25][S:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

参加物

4

反応物 2

HCID 66053N,N-DimethylethylenediamineHCID 21931260Benzyl 4-(chlorosulfonyl)piperidine-1-carboxylate

生成物 1

HCID 66698082Benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylate収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 430 mg (1.35 mmol) of benzyl 4-(chlorosulfonyl)-1-piperidinecarboxylate in 10 mL THF was treated with a 5-fold excess of N,N-dimethylethylenediamine and the mixture was stirred at room temperature for 2 hrs. The THF was removed under vacuum. After dilution with water, the product was extracted with CH2Cl2 and dried. Chromatography on alumina, eluting with EtOAc, gave 450 mg (90% yield) of benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylate as an oil: 1H NMR (CDCl3) δ 7.40-7.30 (m, 5H), 5.13 (s, 2H), 4.33 (m, exchangeable with D2O, 1H), 3.16 (m, 2H), 3.04 (tt, J=11.9, 3.7 Hz, 1H), 2.81 (br t, J=11.9 Hz, 1H), 2.43 (m, 2H), 2.22 (s, 6H), 2.12 (br d, J=12.8 Hz, 2H), 1.74 (ddd, J=25.0, 12.6, 4.5 Hz, 2H).

後処理

  1. customThe THF was removed under vacuum
  2. extractionAfter dilution with water, the product was extracted with CH2Cl2
  3. customdried
  4. washChromatography on alumina, eluting with EtOAc

出典と根拠

ORDレコード
ord-a629bee584d74bba86271a7599e80b7b
出典データセット
uspto-grants-2015_08
特許番号
US09108980B2

反応ノート

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