4-Chloroaniline → tert-Butyl 4-{[(4-chlorophenyl)amino]carbonyl}piperidine-1-carboxylate

HRID 20273

反応式

HRID 20273 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(#N)C>[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:13][CH2:12]2)=[O:16])=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 29201912tert-Butyl 4-{[(4-chlorophenyl)amino]carbonyl}piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1-BOC-piperidine-4-carboxylic acid (100 g, 437 mmol), 4-chloroaniline (61.2 g, 480 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (100 g, 524 mmol) and triethylamine (182.6 mL, 1.31 mol) were dissolved in cold (10° C.) acetonitrile (1.75 L). The reaction mixture was stirred for 54 hours at room temperature and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and then partitioned with 2N hydrochloric acid. The resulting precipitate was filtered off, re-dissolved in dichloromethane, the solution was dried over MgSO4 and evaporated under reduced pressure. The residue was triturated with ether to afford the desired compound as a white solid.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. custompartitioned with 2N hydrochloric acid
  4. filtrationThe resulting precipitate was filtered off
  5. dissolutionre-dissolved in dichloromethane
  6. dry with materialthe solution was dried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-41a1e14ffd1d4ff2a1dd973b7f136e76
出典データセット
uspto-grants-2010_06
特許番号
US07745630B2

関連ノート

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