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Diisopropylethylamine → 3-[1-(4-Chloro-phenyl)-piperidin-4-yl]-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-propan-1-one

HRID 511182
ノート
印刷プレビュー

反応式

HRID 511182 の反応式
[Li+].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C:17]([O-:19])=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.F[P-](F)(F)(F)(F)F.CN(C)C(ON1C2C=CC=CC=2N=N1)=[N+](C)C.Cl.[N+:45]([C:48]1[CH:53]=[CH:52][C:51]([NH:54][CH:55]2[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)=[CH:50][C:49]=1[C:61]([F:64])([F:63])[F:62])([O-:47])=[O:46].C(N(C(C)C)CC)(C)C.[O-2].[Al+3].[O-2].[O-2].[Al+3]>O1CCCC1.CN(C)C=O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([CH2:15][CH2:16][C:17]([N:58]3[CH2:59][CH2:60][CH:55]([NH:54][C:51]4[CH:52]=[CH:53][C:48]([N+:45]([O-:47])=[O:46])=[C:49]([C:61]([F:62])([F:63])[F:64])[CH:50]=4)[CH2:56][CH2:57]3)=[O:19])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 585764893-[1-(4-Chloro-phenyl)-piperidin-4-yl]-propionic acid lithium saltHCID 66671805(4-Nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride

生成物 1

HCID 58576721
3-[1-(4-Chloro-phenyl)-piperidin-4-yl]-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-propan-1-one
収率 24%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-[1-(4-chloro-phenyl)-piperidin-4-yl]-propionic acid lithium salt (14 mg; 0.05 mmol, prepared in accordance with Example 143) in tetrahydrofuran (0.5 mL) is added tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) in dimethylformamide (0.25 mL). A solution of (4-nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride (16 mg; 0.05 mmol, prepared in accordance with Example 8) in dimethylformamide (0.25 mL) and diisopropylethyl amine (25 μL; 0.15 mmol) are then added and the reaction is stirred. After 3 hours at room temperature, aluminium oxide (90 active basic) is added and stirring is continued for 40 minutes. The solids are removed by filtration and the filtrate is concentrated under high vacuum. The obtained residue is purified by preparative HPLC to afford the desired compound (6 mg; 0.012 mmol). The structure was confirmed using Protocol I-D. Calculated mass=539; observed mass=539; HPLC retention time=1.88 min.

後処理

  1. stirringstirring
  2. waitis continued for 40 minutes
  3. customThe solids are removed by filtration
  4. concentrationthe filtrate is concentrated under high vacuum
  5. customThe obtained residue is purified by preparative HPLC

出典と根拠

ORDレコード
ord-29851b90623542dbac0442e9a96b51ac
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096524B2

反応ノート

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