Benzaldehyde → HCID 12348663, compound

HRID 1808146Notes

Reaction equation

HRID 1808146 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([CH2:12][C:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1)C.Cl>CN(C)C=O.O>[NH:15]1[C:16]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:13]([CH2:12][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:14]1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 6890Gramine

Product 1

HCID 12348663HCID 12348663, compoundYield 131.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

NaCN (1.4 g, 29 mmol) was provided in absolute dimethylformamide (10 ml) in argon. At a bath temperature of 35° C. benzaldehyde (3 ml, 29 mmol) dissolved in absolute dimethylformamide (10 ml) was added in drops within 1.5 h and stirred for a further 0.5 h at this temperature. Gramine (10.1 g, 58 mmol) dissolved in absolute dimethylformamide (30 ml) was added in drops to this reaction solution within 2 h at an inside temperature of 70° C. The mixture was stirred a further 1 h at this temperature. For work up the vessel contents were placed in water (150 ml). The aqueous phase was acidified with 2N HCl to separate non-converted gramine as, a water-soluble hydrochloride. The aqueous phase was then extracted with chloroform (3×50 ml). The combined extracts were washed with NaHCO3 solution (50 ml) and dried over Na2SO4. The volatile constituents were then completely removed in a vacuum. The residue (9 g) obtained after distilling off the solvent was purified by column chromatography [silica gel 60 (300 g); cyclohexane/ethyl acetate 6:1 (1500 ml)].

Workup

  1. additionwas added in drops within 1.5 h
  2. additionwas added in drops to this reaction solution within 2 h at an inside temperature of 70° C
  3. stirringThe mixture was stirred a further 1 h at this temperature
  4. customto separate non-converted gramine as, a water-soluble hydrochloride
  5. extractionThe aqueous phase was then extracted with chloroform (3×50 ml)
  6. washThe combined extracts were washed with NaHCO3 solution (50 ml)
  7. dry with materialdried over Na2SO4
  8. customThe volatile constituents were then completely removed in a vacuum

Sources & evidence

ORD record
ord-6cbb0d6e89194ed4b3f1253b5d0505b1
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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