Tert-Butylamine → HCID 23346474, compound

HRID 1856285Notes

Reaction equation

HRID 1856285 reaction equation
[CH2:1]([Li])CCC.[I-].C[S+](C)C.[C:11]12([CH2:25][CH2:24][CH2:23][CH2:22]1)[C:19]1[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:13]([CH:20]=[O:21])=[CH:12]2.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>CCCCCC.O1CCCC1.O>[C:26]([NH:30][CH2:1][CH:20]([C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2([CH2:22][CH2:23][CH2:24][CH2:25]2)[CH:12]=1)[OH:21])([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 6385Tert-ButylamineHCID 75127Trimethylsulfonium iodideHCID 23346462HCID 23346462, compoundHCID 178418339Butyllithium

Product 1

HCID 23346474HCID 23346474, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of n-butyllithium in hexane (6 ml of a 2 M solution) is added dropwise under nitrogen to a stirred suspension of powdered trimethylsulphonium iodide in anhydrous tetrahydrofuran (30 ml) at 0° C. After stirring for 5 minutes, a solution of spiro(cyclopentane-1,1'-indene)-3'-carbaldehyde (2.0 g) in tetrahydrofuran (25 ml) is added. Stirring is continued at 0° C. for 1 hour, whereupon tert.-butylamine (1.0 g) is added and the mixture is allowed to come to about 20° C. After 24 hours, water (200 ml) is added and the solution is extracted three times with diethyl ether. The combined extracts are washed, dried and concentrated to about 50 ml. An excess of hydrogen chloride is added and the precipitated salt is collected and crystallized from ethanol; m.p. 292° C.

Workup

  1. stirringStirring
  2. additionis added
  3. customto come to about 20° C
  4. waitAfter 24 hours
  5. extractionthe solution is extracted three times with diethyl ether
  6. washThe combined extracts are washed
  7. customdried
  8. concentrationconcentrated to about 50 ml
  9. additionAn excess of hydrogen chloride is added
  10. customthe precipitated salt is collected
  11. customcrystallized from ethanol

Sources & evidence

ORD record
ord-34834ca2d9dd48c2ac0ffa3fc8a84f8b
Source dataset
uspto-grants-1980_08
Patent number
US04218472

Reaction notes

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