2-Bromopropane → HCID 16243895, compound

HRID 1636383Notes

Reaction equation

HRID 1636383 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:11]([OH:13])=[O:12])[NH:2]1.Br[CH:15]([CH3:17])[CH3:16].[OH-].[Na+]>C(O)C>[CH:15]([N:2]1[CH:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 63582-Bromopropane2×HCID 14798Sodium Hydroxide2×HCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 16243895HCID 16243895, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-3-isoquinoline-carboxylic acid (9 g, 42 mmol), 2-bromopropane (8 ml, 84 mmol) and 1N NaOH (168 mmol) in ethanol (170 ml) was refluxed for 5 hours, then 2-bromopropane (8 ml, 84 mmol) and 1N NaOH (168 ml, 168 mmol) were added and the mixture was refluxed for 5 hours. Ethanol was removed and the aqueous solution was treated with 6N hydrochloric acid to pH=7. Unreacted starting material was recovered by filtration and the solvent was removed under reduced pressure. The crude was dissolved in ethanol, the inorganics salts were filtered off and the organic solution was evaporated under reduced pressure. This procedure was repeated three times yielding 8.1 g (yield 87%) of pure N-isopropyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid which was used for the next step without further purification.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customEthanol was removed
  3. additionthe aqueous solution was treated with 6N hydrochloric acid to pH=7
  4. filtrationwas recovered by filtration
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe crude was dissolved in ethanol
  7. filtrationthe inorganics salts were filtered off
  8. customthe organic solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-227f563834b1475f97f7eb570b4e2dd6
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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