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

HRID 264705

反応式

HRID 264705 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bbbb513c7a0e4f06ada0d0140c4f7b77
出典データセット
uspto-grants-1997_07
特許番号
US05646144

関連ノート

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