Propylamine → [3-(4-Nitro-3-propylaminomethyl-phenoxy)-phenyl]-carbamic acid benzyl ester

HRID 390236Notes

Reaction equation

HRID 390236 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH:27]=O)[CH:19]=2)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]([NH2:33])[CH2:31][CH3:32].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:1]([O:8][C:9](=[O:29])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH2:27][NH:33][CH2:30][CH2:31][CH3:32])[CH:19]=2)[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58625118[3-(3-Formyl-4-nitro-phenoxy)-phenyl]-carbamic acid benzyl ester

Product 1

HCID 58625058[3-(4-Nitro-3-propylaminomethyl-phenoxy)-phenyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of [3-(3-formyl-4-nitro-phenoxy)-phenyl]-carbamic acid benzyl ester (0.038 mol) in DCE (300 mL) was cooled in an ice bath to 15° C., then propylamine (0.042 mol), followed by NaBH(OAc)3 (0.057 mol) which was added portionwise. The reaction mixture was stirred overnight at room temperature and the mixture was washed with a saturated NaHCO3 solution. The organic layer was separated, dried (MgSO4), filtered off and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: 90:10 CH2Cl2:CH3OH). The product fractions were collected and the solvent was evaporated, then co-evaporated with toluene to yield the title compound as a residue.

Workup

  1. additionwas added portionwise
  2. washthe mixture was washed with a saturated NaHCO3 solution
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered off
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: 90:10 CH2Cl2:CH3OH)
  8. customThe product fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2228fd790e1a4f3caa7f89a0abdd1158
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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