Benzoic Acid → 1-Phenyl-1-{4-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperazin-1-yl}-methanone

HRID 1434578ノート

反応式

HRID 1434578 の反応式
C1(N=C=N)CCCCC1.[C:10]([OH:18])(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.Cl.[N:33]1([CH2:39][CH2:40][CH2:41][O:42][C:43]2[CH:55]=[CH:54][C:46]([CH2:47][N:48]3[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]3)=[CH:45][CH:44]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[C:11]1([C:10]([N:51]2[CH2:52][CH2:53][N:48]([CH2:47][C:46]3[CH:45]=[CH:44][C:43]([O:42][CH2:41][CH2:40][CH2:39][N:33]4[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]4)=[CH:55][CH:54]=3)[CH2:49][CH2:50]2)=[O:18])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

8

反応物 5

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 12048208N-CyclohexylcarbodiimideHCID 687034951-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-piperazine trihydrochloride

生成物 1

HCID 579357461-Phenyl-1-{4-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperazin-1-yl}-methanone収率 77.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

N-Cyclohexylcarbodiimide, N-methyl polystyrene HL (200-400 mesh) 1.8 mMol/g (650 mg, 1.172 mmol) was suspended in a (1:1) mixture of dichloromethane and dimethylformamide and treated sequentially with benzoic acid (72 mg, 0.58 mmol), 1-hydroxybenzotriazole hydrate (80 mg, 0.58 mmol) and stirred for 10 minutes at room temperature. A solution of 1-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperazine trihydrochloride (D2) (125 mg, 0.29 mmol) in dichloromethane (1 ml) and triethylamine (0.13 ml, 0.87 mmol) was then added to the reaction and stirred at room temperature for 16 hours. After filtration, the filtrate was applied to a Mega Bond elute SCX ion exchange column washing sequentially with water and methanol, followed by 0.880 ammonia/methanol (1:10) to elute the crude reaction mixture. Purification by silica gel chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.5:4.5:95) to afford the title product (95 mg, 77%); MS (ES+), m/e 422 [M+H]+.

後処理

  1. stirringstirred at room temperature for 16 hours
  2. filtrationAfter filtration
  3. washelute SCX ion exchange column
  4. washwashing sequentially with water and methanol
  5. washto elute the crude
  6. customreaction mixture
  7. customPurification by silica gel chromatography
  8. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.5:4.5:95)

出典と根拠

ORDレコード
ord-428d829494f948a59d4af8d2e852fa8a
出典データセット
uspto-grants-2009_11
特許番号
US07615550B2

反応ノート

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