Hydrochloric Acid → (2R*,4S*)-2-(4-Chlorobenzyl)-1-(3,5-dimethylbenzoyl)-N-(4-quinolinylmethyl)-4-piperidinamine

HRID 264705

반응식

HRID 264705 반응식
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C@@H:7]2[CH2:12][C@@H:11]([NH2:13])[CH2:10][CH2:9][N:8]2[C:14](=[O:23])[C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=2)=[CH:4][CH:3]=1.[N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH:36]=O)=[CH:28][CH:27]=1.B([O-])=O.[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]2[CH2:12][C@@H:11]([NH:13][CH2:36][C:29]3[C:30]4[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:26]=[CH:27][CH:28]=3)[CH2:10][CH2:9][N:8]2[C:14](=[O:23])[C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=2)=[CH:24][CH:25]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 780724-QuinolinecarboxaldehydeHCID 145326Sodium metaborateHCID 57322251(2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethylbenzoyl)-4-piperidinamine

생성물 1

HCID 44334143(2R*,4S*)-2-(4-Chlorobenzyl)-1-(3,5-dimethylbenzoyl)-N-(4-quinolinylmethyl)-4-piperidinamine수율 41.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 550 mg (1.54 mmol) of (2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethyl-benzoyl)-4-piperidinamine and 242 mg(1.54 mmol) of 4-quinolinecarboxaldehyde are dissolved in 30 ml of toluene and evaporated to dryness under reduced pressure. This is repeated twice more. The residue is taken up in 10 ml of ethanol, 70 mg (1.85 mmol) of sodium boranate are added and the mixture is stirred at 25° for 3 hours. It is acidified with 1N hydrochloric acid and left to stir for 1 hour. The reaction mixture is poured into saturated aqueous sodium carbonate solution and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness under reduced pressure. The crude product is recrystallised twice from ethyl acetate and yields 320 mg of the title compound of the formula ##STR110## in the form of white crystals; melting point 148°-9°; MS:M+497.

후처리

  1. customevaporated to dryness under reduced pressure
  2. waitleft
  3. stirringto stir for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe crude product is recrystallised twice from ethyl acetate

출처 및 근거

ORD 기록
ord-bbbb513c7a0e4f06ada0d0140c4f7b77
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646144

연결된 노트

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