Allylamine → HCID 18324837, compound

HRID 1250884Notes

Reaction equation

HRID 1250884 reaction equation
C(N)C=C.[CH2:5]([N:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[CH3:21])C1=S)[CH:6]=[CH2:7]>ClCCl>[CH2:5]([NH:8][CH2:13][CH2:12][CH2:11][NH:10][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH3:21])[CH:6]=[CH2:7]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 9925710HCID 9925710, compound

Product 1

HCID 18324837HCID 18324837, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of allylamine (1.0 mL) and the hydrobromide salt of Step B (1.0 g) was heated at 100° C. under nitrogen for 45 minutes. The reaction was cooled and partitioned between dichloromethane and 1 N sodium hydroxide. The aqueous layer was extracted with dichloromethane, the extracts were dried over sodium sulfate and concentrated in vacuo to give a yellow oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 98:2 dichloromethane-methanol to 90:10 dichloromethane-methanol containing 0.2% ammonium hydroxide) provided the title compound (0.35 g, 50.5%) as a yellow oil which was used as such in the next step.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between dichloromethane and 1 N sodium hydroxide
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customabsorbed onto a column of Merck-60 flash silica gel
  8. washElution with a solvent gradient (from 98:2 dichloromethane-methanol to 90:10 dichloromethane-methanol containing 0.2% ammonium hydroxide)

Sources & evidence

ORD record
ord-0d58197aad7844aaad633503b11167da
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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