4-Aminobenzoic Acid → Tert-butyl 4-((4-aminobenzamido)methyl)piperidine-1-carboxylate

HRID 1410485ノート

反応式

HRID 1410485 の反応式
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[NH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>ClCCl>[NH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)=[O:22])=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 9784-Aminobenzoic AcidHCID 79724-MethylmorpholineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 59587665Tert-butyl 4-((4-aminobenzamido)methyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-(aminomethyl)-Boc-piperidine (0.313 g, 1.458 mmol), 4-aminobenzoic acid (0.200 g, 1.458 mmol) and N-methyl morpholine (0.242 mL, 2.187 mmol) in dichloromethane (2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.422 g, 2.187 mmol) and the reaction mixture stirred at room temperature overnight. The reaction was then washed with water and brine. The organic phase was dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel column chromatography using a 0-100% EtOAc in hexane gradient to afford tert-butyl 4-((4-aminobenzamido)methyl)piperidine-1-carboxylate. LCMS (3) Rt: 1.91 min; m/z (ES+) 334.

後処理

  1. washThe reaction was then washed with water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fbd474f4f07f4e85a65752ee813c1cdf
出典データセット
uspto-grants-2014_12
特許番号
US08921544B2

反応ノート

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