Hydrochloric Acid → (+/-)-trans-[2-(4-Morpholinyl)cyclohexyl](4-nitrophenyl)acetate monohydrochloride

HRID 566230

反応式

HRID 566230 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](CC([Cl:13])=O)=[CH:6][CH:5]=1)([O-])=O.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:18]=1)([O-:16])=[O:15].Cl.[CH3:28][CH2:29][O:30][CH2:31][CH3:32]>C(Cl)(Cl)Cl>[ClH:13].[N:1]1([C@@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]2[CH:23]([C:20]2[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=2)[C:24]([OH:26])=[O:25])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2 回HCID 4661(4-Nitrophenyl)acetic acidHCID 6452210Benzeneacetyl chloride, 4-nitro-

生成物 1

HCID 21308429(+/-)-trans-[2-(4-Morpholinyl)cyclohexyl](4-nitrophenyl)acetate monohydrochloride

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

4-Nitrophenylacetyl chloride, prepared according to the method described in Example 8 using 4-nitrophenylacetic acid (5.4 g, 29.8 mmol), is dissolved in chloroform (15 mL). This solution is refluxed for 9 hours with a solution of (±)-trans-[2-(4-morpholinyl)]cyclohexanol (5.25 g, 28.3 mmol) in chloroform (15 mL) under nitrogen. The solvent is removed in vacuo, and the residue is partitioned between 1M hydrochloric acid (60 mL) and ether (50 mL). The ether layer is separated and the aqueous layer is washed with more ether (2×50 mL), and then basified by the addition of 50% sodium hydroxide solution. This is then extracted with ether (5×60 mL), and the combined ether extracts are washed repeatedly with water to remove any unreacted aminoalcohol. The ether containing the product is then dried over sodium sulfate, and the solvent is removed to leave the crude free ester. The residue is dissolved in ether (20 mL) and treated with HCl in ether to precipitate the salt. It is washed with ether and recrystallised from hot methanol to yield the title compound.

後処理

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between 1M hydrochloric acid (60 mL) and ether (50 mL)
  3. customThe ether layer is separated
  4. washthe aqueous layer is washed with more ether (2×50 mL)
  5. additionbasified by the addition of 50% sodium hydroxide solution
  6. extractionThis is then extracted with ether (5×60 mL)
  7. washthe combined ether extracts are washed repeatedly with water
  8. customto remove any unreacted aminoalcohol
  9. dry with materialThe ether containing the product is then dried over sodium sulfate
  10. customthe solvent is removed
  11. customto leave the crude free ester
  12. customto precipitate the salt
  13. washIt is washed with ether
  14. customrecrystallised from hot methanol

出典と根拠

ORDレコード
ord-7bbf983c8da1439d9bcc0fb08b667e5b
出典データセット
uspto-grants-2001_01
特許番号
US06174879B1

関連ノート

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