Hydrochloric Acid → 2-(butylamino)-2-methylpropan-1-ol

HRID 1693638Notes

Reaction equation

HRID 1693638 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].Br[CH2:8][CH2:9][CH2:10][CH3:11].Cl>C(O)(C)C>[CH2:8]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8002Butyl bromideHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 2356402-(butylamino)-2-methylpropan-1-olYield 27%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-amino-2-methylpropan-1-ol (14 g, 157 mmol) in isopropanol (100 ml) was treated with 1-bromobutane (37 g, 272 mmol). The mixture was refluxed for 12 hrs, treated with 8 ml of concentrated HCl, then distilled to remove volatiles. The remaining residue was basified with 20% of NaOH, and extracted with Et2O (2×). The Et2O layers were combined and distilled to afford 6.1 g (27%) of the title compound (124-126° C. @54-56 Torr). 1H NMR (400 MHz, CDCl3) δ ppm 0.92 (t, J=7.36 Hz, 3H) 1.06 (s, 6H) 1.10 (s, 1H) 1.29-1.50 (m, 4H) 2.49 (t, J=6.75 Hz, 2H) 3.28 (s, 2H).

Workup

  1. temperatureThe mixture was refluxed for 12 hrs
  2. distillationdistilled
  3. customto remove volatiles
  4. extractionextracted with Et2O (2×)
  5. distillationdistilled

Sources & evidence

ORD record
ord-f451bd3435e343f0ae12b030339c8605
Source dataset
uspto-grants-2012_04
Patent number
US08158663B2

Reaction notes

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