Diisopropylethylamine → N-(2-cyclohexyl-1-pyridin-2-ylethyl)-5-methyl-1,3-benzoxazol-2-amine

HRID 52572Notes

Reaction equation

HRID 52572 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@H:7]([NH2:15])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl[C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:20]=2[N:21]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH:9]1([CH2:8][CH:7]([NH:15][C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:20]=3[N:21]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98156341-(+)-(S)-(2-pyridyl)-2-cyclohexylethylamineHCID 99896072-Chloro-5-methyl-1,3-benzoxazole

Product 1

HCID 6916044N-(2-cyclohexyl-1-pyridin-2-ylethyl)-5-methyl-1,3-benzoxazol-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 132.8 g (0.65 moles) 1-(+)-(S)-(2-pyridyl)-2-cyclohexylethylamine in 550 mL methylene chloride was added 109 g (0.65 moles) 2-chloro-5-methylbenzoxazole followed by 168 g (1.3 moles) diisopropylethylamine. The reaction mixture was heated to reflux for 5-40 hours, cooled and concentrated under reduced pressure. The mixture was dissolved in 2 L of ethanol. Addition of 2-3 L of water gave crude [(2-cyclohexyl-1-(2-pyridyl)ethylamino]-5-methylbenzoxazole. Recrystallization from ethanol/water gave 190 g (83%) as a hydrate; mp 80°-86° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5-40 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe mixture was dissolved in 2 L of ethanol
  6. additionAddition of 2-3 L of water

Sources & evidence

ORD record
ord-f78597140ae842a8a39561bc261743da
Source dataset
uspto-grants-1997_04
Patent number
US05616717

Reaction notes

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