Allylamine → HCID 18324818, compound

HRID 1250891Notes

Reaction equation

HRID 1250891 reaction equation
C(N)C=C.[CH2:5]([N:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[C:19]([Cl:20])=[CH:18][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[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])[CH:6]=[CH2:7]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 9925711HCID 9925711, compound

Product 1

HCID 18324818HCID 18324818, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of allylamine (20 mL) and the hydrobromide salt of Step B (8.6 g) was heated at 100° C. under nitrogen for 30 minutes. The reaction mixture was cooled and partitioned between dichoromethane and 1N sodium hydroxide. The aqueous layer was extracted with dichloromethane, and the combined organic layers 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 1:1 ethyl acetate-hexane followed by 80:20 dichloromethane-methanol containing 0.2% ammonium hydroxide gave the title compound (5.0 g, 83.8%) as a yellow oil which was used as such in the next step.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between dichoromethane and 1N sodium hydroxide
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe combined organic layers 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 1:1 ethyl acetate-hexane

Sources & evidence

ORD record
ord-faf4fb7ec35f4e2ea285941b710f1b17
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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