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

HRID 20273

반응식

HRID 20273 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41a1e14ffd1d4ff2a1dd973b7f136e76
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745630B2

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