Butylamine → HCID 77752115, compound

HRID 2185683Notes

Reaction equation

HRID 2185683 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C([Li])CCC.CCCCCC.[CH3:17][C:18]1([CH3:32])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]1[C:27](OCC)=[O:28]>C1(C)C=CC=CC=1>[CH2:1]([NH:5][C:27]([CH:19]1[C:18]([CH3:32])([CH3:17])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20]1)=[O:28])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8007ButylamineHCID 8058HexaneHCID 23313846HCID 23313846, compoundHCID 178418339Butyllithium

Product 1

HCID 77752115HCID 77752115, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Butylamine (15 ml) in toluene (40 ml) was cooled to −78° C. and a 2.5M solution of butyllithium in hexane (12.91 ml, 31.5 mmol) was added dropwise. After half an hour, ethyl 3,3-dimethylindoline-2(R/S)-carboxylate (4.600 g, 21 mmol) was added to the solution and this mixture was stirred under nitrogen for three hours. The mixture was then poured into a water/ice mixture (50 ml) and extracted with ethyl acetate; the extracts were dried over magnesium sulphate and the solvent was removed to give a brown oil. This was purified by chromatography on a column of silica gel, using a 7/3 petroleum ether/ethyl acetate mixture as eluent in order to give a yellow solid.

Workup

  1. waitAfter half an hour
  2. extractionextracted with ethyl acetate
  3. dry with materialthe extracts were dried over magnesium sulphate
  4. customthe solvent was removed
  5. customto give a brown oil
  6. customThis was purified by chromatography on a column of silica gel
  7. customto give a yellow solid

Sources & evidence

ORD record
ord-64f36398cec94220b5bb0e25f74e2552
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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