Hydrochloric Acid → HCID 19989934, compound

HRID 1031512Notes

Reaction equation

HRID 1031512 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[CH2:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][CH:5]=1)#[N:2].[H][H].[ClH:21]>[Pd].C(O)(C)C>[ClH:21].[NH2:2][CH2:1][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22619377HCID 22619377, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19989934HCID 19989934, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

t-Butyl p-(cyanomethyl)-phenylacrylate (6.0 g) is combined with 600 mg 10% palladium on carbon in 80 ml isopropanol and 24 ml 1N HCl and treated with hydrogen at room temperature. After 8 hours at 3 atmospheres pressure, the catalyst is filtered off and the filtrate concentrated under vacuum. The residue is triturated with ether, filtered and dried under vacuum to afford t-butyl p-(2-aminoethyl)-phenylpropionate hydrochloride as a white solid. The hydrochloride salt is partitioned between ethyl acetate and 1N NaOH. The ethyl acetate extract is washed with a saturated NaCl solution and dried over MgSO4. Filtration and concentration of the filtrate affords t-butyl p-(2-aminoethyl)-phenylpropionate as a yellow oil; NMR (CDCl3): 7.1 (4H,s), 2.98 (2H,t), 2.89 (2H,t) 2.73 (2H,t), 2.5 (2H,t), 2.02 (2H,s), 1.42 (9H,s).

Workup

  1. filtrationthe catalyst is filtered off
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe residue is triturated with ether
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-bce0592c043b466993ade435e0bff10e
Source dataset
uspto-grants-1990_09
Patent number
US04954504

Reaction notes

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