Potassium Iodide → HCID 131716780、化合物

HRID 981314ノート

反応式

HRID 981314 の反応式
[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Br[CH:31]([CH3:51])[CH2:32][C:33]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:34]([N:36]([CH3:38])[CH3:37])=[O:35]>O.CC(C)CC(=O)C>[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH:31]([CH3:51])[CH2:32][C:33]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:34]([N:36]([CH3:37])[CH3:38])=[O:35])[CH2:11][C@H:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 98616214-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxypiperidin-4-YL]benzamideHCID 20071680HCID 20071680、化合物

生成物 1

HCID 131716780HCID 131716780、化合物収率 31.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

4.71 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide, 3.66 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 15 minutes using a water separator. 6 parts of α-(2-bromopropyl)-N,N-dimethyl-α-phenylbenzeneacetamide were added and stirring was continued for 2.5 hours at reflux. Water was added. The organic layer was separated, washed with a sodium chloride solution, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and crystallized from acetonitrile, yielding 2.83 parts (31.8%) of cis-4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-3-methoxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide; mp. 198.3° C. (compound 54).

後処理

  1. temperaturerefluxed for 15 minutes
  2. temperatureat reflux
  3. customThe organic layer was separated
  4. washwashed with a sodium chloride solution
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe product was filtered off
  13. customcrystallized from acetonitrile

出典と根拠

ORDレコード
ord-a8a69f9422ff49d987c092218e1a0606
出典データセット
uspto-grants-1991_02
特許番号
US04990521

反応ノート

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