(+/-)-Cis-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic Acid Benzyl Ester → (+/-)-cis-1-(4-Dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-aminoquinoline

HRID 1785887Notes

Reaction equation

HRID 1785887 reaction equation
C(OC(=O)[NH:10][C@H:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21](=[O:31])[C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=2)[C@@H:13]([CH3:32])[CH2:12]1)C1C=CC=CC=1>C(O)C>[CH3:30][N:28]([CH3:29])[C:25]1[CH:24]=[CH:23][C:22]([C:21]([N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C@H:11]([NH2:10])[CH2:12][C@@H:13]2[CH3:32])=[O:31])=[CH:27][CH:26]=1

Participants

3

Reactant 1

HCID 86592021(+/-)-Cis-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic Acid Benzyl Ester

Product 1

HCID 68921648(+/-)-cis-1-(4-Dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-aminoquinolineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-Cis-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic acid benzyl ester (665 mg, 1.49 mmol) was dissolved in ethanol (30 mL). The resulting solution was evacuated and backfilled with argon. A catalytic amount of palladium on carbon (10%) was added. The vessel was once again evacuated and this time was backfilled with hydrogen from a balloon. The reaction was then allowed to react at room temperature over night under a hydrogen atmosphere. Reaction was complete after 18 h. The mixture was carefully filtered and concentrated to 10% volume. The resulting concentrated solution was filtered through an Acrodisc® and concentrated to afford the crude amine (423 mg, 92%).

Workup

  1. customThe resulting solution was evacuated
  2. additionA catalytic amount of palladium on carbon (10%) was added
  3. customThe vessel was once again evacuated
  4. customto react at room temperature over night under a hydrogen atmosphere
  5. customReaction
  6. filtrationThe mixture was carefully filtered
  7. concentrationconcentrated to 10% volume
  8. filtrationThe resulting concentrated solution was filtered through an Acrodisc®
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4e4a6aa273e64d5ea72cc4632fb25e8e
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…