3-Amino-1-propanol → N-(3-Hydroxypropyl)trifluoroacetamide
Reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[NH2:10][CH2:11][CH2:12][CH2:13][OH:14].C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>>[OH:14][CH2:13][CH2:12][CH2:11][NH:10][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Ethyl trifluoroacetate (14.1 g; 0.1 mol) was added dropwise to 3-amino-1-propanol (6 g; 0.08 mol) cooled to 0° C. The mixture was stirred at 0° C. for 60 min; the completion of the reaction was confirmed by a negative Ninhydrin test. Volatiles were removed by rotary evaporation and the residue purified by vacuum distillation to provide N-(3-hydroxypropyl)trifluoroacetamide as a clear, viscous liquid in a yield of 13.4 g (98%). 1H-NMR (500 MHz, CDCl3): δ=3.52-3.57 ppm (m, 2H), 2.17 ppm (bs, 1H), 3.54 ppm (dt, J=6.0, 6.0 Hz, 2H), 3.81 ppm (t, J=5.5 Hz, 2H), 7.28 ppm (bs, 1H), 13C-NMR (500 MHz, CDCl3): δ=30.42, 38.35, 61.05, 115.93 ppm (q, J=1142 Hz), 157.76 ppm (q, J=150 Hz).
Workup
- customVolatiles were removed by rotary evaporation
- distillationthe residue purified by vacuum distillation
Sources & evidence
- ORD record
- ord-4cd858982cf945d8925dcb0dd5c6d2d5
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422232B2
Reaction notes
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