Aniline → HCID 21904394, compound

HRID 1246932Notes

Reaction equation

HRID 1246932 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH:12]2[C:10]([CH:15]=O)([CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH3-]C#N.[Na+]>CC(O)=O.CO>[CH2:1]([N:8]1[CH2:14][CH2:13][CH:12]2[C:10]([CH2:15][NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 21904386HCID 21904386, compound

Product 1

HCID 21904394HCID 21904394, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 3-Benzyl-3-aza-bicyclo[4.1.0]heptane-1-carbaldehyde (174) (300 mg, 1.39 mmol) in 5% HOAc in MeOH (2 ml) was added aniline (0.38 ml, 4.18 mmol) and NaCNBH3 (250 mg, 3.97 mmol). The mixture was stirred at room temperature 2 hrs. MeOH was removed by evaporation. Water (5 mL) was added to the residue. The mixture was neutralized with 2N KOH to pH=10. Extraction with CH2Cl2 (2×10 ml) followed by standard work-up provided crude 175 which was purified by silica gel chromatography (1% MeOH in CH2Cl2). LRMS (calculated for C20H25N2, M+1) 293. found 293.

Workup

  1. customMeOH was removed by evaporation
  2. additionWater (5 mL) was added to the residue
  3. extractionExtraction with CH2Cl2 (2×10 ml)
  4. customprovided crude 175 which
  5. customwas purified by silica gel chromatography (1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-27b3e18433ba4b8393fcd48c55b287c6
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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