Propylamine → HCID 58625119, compound

HRID 1968834Notes

Reaction equation

HRID 1968834 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:15]([NH2:18])[CH2:16][CH3:17].[CH:19]1([CH2:25][NH:26][C:27]2[CH:28]=[C:29]([CH:42]=[CH:43][CH:44]=2)[O:30][C:31]2[CH:32]=[CH:33][C:34]([N+:39]([O-:41])=[O:40])=[C:35]([CH:38]=2)[CH:36]=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCCl>[CH:19]1([CH2:25][NH:26][C:27]2[CH:44]=[CH:43][CH:42]=[C:29]([O:30][C:31]3[CH:32]=[CH:33][C:34]([N+:39]([O-:41])=[O:40])=[C:35]([CH2:36][NH:18][CH2:15][CH2:16][CH3:17])[CH:38]=3)[CH:28]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58625125HCID 58625125, compound

Product 1

HCID 58625119HCID 58625119, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

NaBH(OAc)3 (0.0080 mol) was added to a mixture of propylamine (0.0054 mol) and 5-[3-(cyclohexylmethyl-amino)-phenoxy]-2-nitro-benzaldehyde (0.00054 mol) in DCE (100 mL). Then the reaction mixture was stirred overnight at room temperature and washed with a saturated NaHCO3 solution. The organic layer was separated, dried (MgSO4), and filtered, and the solvent was evaporated. The residue was purified by column chromatography (eluent: 100% CH2Cl2). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. washwashed with a saturated NaHCO3 solution
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (eluent: 100% CH2Cl2)
  7. customThe purest product fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-669b4ca7786f41ed8e752708e231d842
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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