Benzylamine → HCID 86754131, compound

HRID 1416760Notes

Reaction equation

HRID 1416760 reaction equation
C(O[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:5])C.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(O)C>[C:35]1([CH2:34][N:41]([CH2:15][C:13]2[CH:14]=[CH:8][CH:9]=[CH:11][CH:12]=2)[C:4]([C:6]2([C:29]([OH:31])=[O:30])[O:10][C:9]3[CH:11]=[CH:12][C:13]([CH2:15][CH:16]([NH:18][CH2:19][CH:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[OH:21])[CH3:17])=[CH:14][C:8]=3[O:7]2)=[O:5])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 15223305HCID 15223305, compound

Product 1

HCID 86754131HCID 86754131, 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 benzylamine (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 colorless spongy solid; mp 101; yield 2.0 g; 67%; M+H 600.

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 colorless spongy solid

Sources & evidence

ORD record
ord-b451793ade844309ae3bb6f33ab680be
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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