HCID 22380867, compound → HCID 22380830, compound

HRID 1836313Notes

Reaction equation

HRID 1836313 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1([CH3:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[CH3:25][C:9]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1

Participants

4

Reactant 1

HCID 22380867HCID 22380867, compound

Product 1

HCID 22380830HCID 22380830, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-Benzyl-1-methyl-1-o-tolyl-1,2,3,4-tetrahydro-isoquinoline (164 mg, 0.50 mmol) and 10% Pd/C (16 mg) in acetic acid (6 ml) is stirred for 5 hours at room temperature under 1 atm of H2. The mixture is filtered through celite and the filtrate concentrated. The residue is diluted with methylene chloride and basified with saturated NaHCO3 to pH 8. The layers are separated and the aqueous layer extracted with methylene chloride. The combined organic layers are washed with brine, dried over sodium sulfate, and concentrated to give 1-Methyl-1-o-tolyl-1,2,3,4-tetrahydro-isoquinoline. 1H NMR (400 MHz, CDCl3) δ 7.62 (d, J=7.2 Hz, 1H), 7.28-6.97 (m, 7H), 6.69 (d, J=8.0 Hz, 1H), 3.43-3.36 (m, 1H), 3.21-3.03 (m, 2H), 2.79 (d, J=16.4 Hz, 1H), 1.99 (s, 3H), 1.91 (s, 3H).

Workup

  1. filtrationThe mixture is filtered through celite
  2. concentrationthe filtrate concentrated
  3. additionThe residue is diluted with methylene chloride and basified with saturated NaHCO3 to pH 8
  4. customThe layers are separated
  5. extractionthe aqueous layer extracted with methylene chloride
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ad9d83b75ec44eabbf93477cb3d24420
Source dataset
uspto-grants-2004_08
Patent number
US06777422B2

Reaction notes

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