Potassium Carbonate → Tert-butyl 3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propylcarbamate

HRID 2085394

反応式

HRID 2085394 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.Br[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+].C(N(C(C)C)CC)(C)C>O1CCOCC1>[C:14]([NH:13][C:9]1[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][N:1]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:2][CH2:3]2)[CH:12]=[CH:11][CH:10]=1)(=[O:16])[CH3:15]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 22048943Acetamide, N-[3-(4-piperidinyl)phenyl]-

生成物 1

HCID 22049023Tert-butyl 3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propylcarbamate収率 431.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A solution of N1-[3-(4-piperidyl)phenyl]acetamide (550 mg, 0.210 mmol), tert-butyl N-(3-bromopropyl)-carbamate (550 mg, 0.230 mmol), K2CO3 (1.10 g, 0.890 mmol), diisopropylethyl amine (1.50 mL) and a few crystals of KI in dioxane (20 mL) was heated at reflux temperature for 2 days. The precipitated salts were removed by filtration, concentrated in vacuo and the crude product was chromatographed, giving the desired product (340 mg). 1H NMR δ 8.15 (s, 1 H), 7.47-7.44 (m, 2 H), 7.22 (t, 1 H, J=7.8 Hz), 6.94 (d, 1 H, J=7.8 Hz), 5.53 (b, 1 H), 3.23 (b, 6 H), 2.80-1.60 (m, 9 H), 2.20 (s, 3 H), 1.45 (s, 9 H).

後処理

  1. temperatureat reflux temperature for 2 days
  2. customThe precipitated salts were removed by filtration
  3. concentrationconcentrated in vacuo
  4. customthe crude product was chromatographed

出典と根拠

ORDレコード
ord-20df3ef2162b4b60b6c9f8b40e867431
出典データセット
uspto-grants-2004_04
特許番号
US06720324B2

関連ノート

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