Propylamine → HCID 57447007, compound

HRID 2366586Notes

Reaction equation

HRID 2366586 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C[Al](C)C.[CH2:9]([C:12]1[N:13]([CH2:25][CH2:26][CH2:27][C:28](OCC)=[O:29])[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1)[CH2:10][CH3:11]>ClCCl.C1(C)C=CC=CC=1>[CH2:1]([NH:4][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][N:13]1[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=[C:12]1[CH2:9][CH2:10][CH3:11])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 7852PropylamineHCID 16682925TrimethylaluminumHCID 57447006HCID 57447006, compound

Product 1

HCID 57447007HCID 57447007, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of n-propylamine (3.0 mL, 36 mmol) in dichloromethane (75 mL) was cooled to 0° C.; trimethylaluminum (available as a 2 M solution in toluene, 18 mL, 36 mmol) was added dropwise with stirring over a period of three minutes. The reaction was stirred for one hour at 0° C. and 30 minutes at ambient temperature. A solution of ethyl 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanoate (5.80 g, 17.8 mmol, prepared as described in Parts A-D of Example 1) in dichloromethane (30 mL) was added, and the reaction was then heated at reflux for three days. The work-up procedure described in Part E of Example 1 was followed to provide N-propyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide as a brown oil.

Workup

  1. stirringThe reaction was stirred for one hour at 0° C. and 30 minutes at ambient temperature
  2. temperaturethe reaction was then heated
  3. temperatureat reflux for three days

Sources & evidence

ORD record
ord-4f342f6158a14874ab63793fb3e5efcf
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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