Propylamine → HCID 58625080, compound

HRID 390256Notes

Reaction equation

HRID 390256 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH2:5]([O:12][C:13](=[O:39])[N:14]([CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24](C=O)[CH:23]=2)[CH:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:42](C)=O.[Na+].[OH-].[Na+]>ClCCCl>[CH2:5]([O:12][C:13](=[O:39])[N:14]([CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([CH2:42][NH:4][CH2:1][CH2:2][CH3:3])[CH:23]=2)[CH:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 58625104HCID 58625104, compound

Product 1

HCID 58625080HCID 58625080, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of propylamine (0.00356 mol) in DCE (70 mL) was stirred at room temperature. Cyclohexyl-[3-(3-formyl-4-nitro-phenoxy)-phenyl]-carbamic acid benzyl ester (0.00274 mol) was added. NaBH(OAc)3 (0.00438 mol) was added. The reaction mixture was stirred overnight at room temperature. A 10% NaOH solution was added and this mixture was extracted with diisopropyl ether. The separated organic layer was dried (MgSO4), filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: 100:0 to 96:4 CH2Cl2:CH3OH). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionthis mixture was extracted with diisopropyl ether
  3. dry with materialThe separated organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: 100:0 to 96:4 CH2Cl2:CH3OH)
  7. customThe product fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-22f7f6433e6a4a41853e9c4d0d3acd90
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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