Butylamine → HCID 67587984, compound

HRID 1416759Notes

Reaction equation

HRID 1416759 reaction equation
C([O:3][C:4]([C:6]1([C:29]([O:31]CC)=[O:30])[O:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][CH:16]([NH:18][CH2:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[OH:21])[CH3:17])=[CH:14][C:8]=2[O:7]1)=O)C.[CH2:34]([NH2:38])[CH2:35][CH2:36][CH3:37]>C(O)C>[CH2:34]([N:38]([CH2:14][CH2:8][CH2:9][CH3:11])[C:4]([C:6]1([C:29]([OH:31])=[O:30])[O:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][CH:16]([NH:18][CH2:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[OH:21])[CH3:17])=[CH:14][C:8]=2[O:7]1)=[O:3])[CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 15223305HCID 15223305, compound

Product 1

HCID 67587984HCID 67587984, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl)-benzo-[1,3]dioxole-2,2-dicarboxylic acid bis-ethyl ester (2.4 g, 5 mmol) and n-butylamine (10 mL, excess) was refluxed in ethanol for 48 h. The reaction mixture was concentrated and the residue obtained was extracted with chloroform:methanol (3:1). It was washed with water and dried over anhydrous MgSO4. The organic layer was filtered and concentrated. The residue obtained was chromatographed over silica gel eluted with 9:1 chloroform:methanol to yield a brown semi solid; yield 1.6 g; 61%; M+H 532.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue obtained
  3. extractionwas extracted with chloroform:methanol (3:1)
  4. washIt was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationThe organic layer was filtered
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customwas chromatographed over silica gel
  10. washeluted with 9:1 chloroform
  11. custommethanol to yield a brown semi solid

Sources & evidence

ORD record
ord-df8d7f3c5fc640ef832bf65699433d4b
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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