Triethylamine → HCID 10800464, compound

HRID 266162Notes

Reaction equation

HRID 266162 reaction equation
Cl[C:2]1[C:3]([N+:19]([O-])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.CCN(CC)CC>CO.N.[Pd]>[NH2:19][C:3]1[CH:2]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 19032654HCID 19032654, compound

Product 1

HCID 10800464HCID 10800464, compoundYield 48.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A mixture of 3b (1.65 g), Pd/C (0.8 g) and Et3N (6 ml) in MeOH (70 ml) was hydrogenated at 36 psi in a Parr apparatus for 5 hours. The mixture was filtered through celite and the solvent was evaporated to yield 2.5 g of the raw product, which was suspended in diluted ammonia and extracted three times with Et2O. The combined organic extracts were dried (MgSO4), filtered and evaporated to yield 0.63 g (48%) of pure 7-amino-2-(N,N-di-n-propylamino)tetralin (4b).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent was evaporated
  3. customto yield 2.5 g of the raw product, which
  4. extractionextracted three times with Et2O
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4897f799c2ea4e5fb75fe25920d576b3
Source dataset
uspto-grants-1997_07
Patent number
US05650427

Reaction notes

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