Isobutylamine → HCID 18324831, compound

HRID 1250895Notes

Reaction equation

HRID 1250895 reaction equation
[CH2:1](N)C(C)C.[CH2:6]([N:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[CH3:22])C1=S)[CH:7]=[CH2:8]>ClCCl>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([CH3:22])=[C:15]([NH:11][CH2:12][CH2:13][CH2:14][NH:9][CH2:6][CH:7]([CH3:8])[CH3:1])[CH:20]=1

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 9925710HCID 9925710, compound

Product 1

HCID 18324831HCID 18324831, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of isobutylamine (27.2 mL) and the hydrobromide salt of Example 8, Step B (9.4 g) was heated at 90° C. under nitrogen for 1 hour. The reaction was cooled and partitioned between dichloromethane and 1N sodium hydroxide. The aqueous layer was extracted with dichloromethane, and the combined extracts were dried over sodium sulfate and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with 25% ethyl acetate in hexane followed by 80:20 dichloromethane-methanol containing 0.2% ammonium hydroxide gave the title compound (6.0 g, 85.9%) as a brown oil, which was used as such in the next step.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between dichloromethane and 1N sodium hydroxide
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customabsorbed onto a column of Merck-60 flash silica gel
  8. washElution with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-28b1dc59f01c4f30a988c2ba1176930c
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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