3-(3,5-Bis(trifluoromethyl)benzylamino)propanol → N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-hydroxyethyl)amine
Reaction equation
ClC1C([C:8](O)=[O:9])=C(C2C=CC=CC=2)C(C)=CN=1.[F:18][C:19]([F:37])([F:36])[C:20]1[CH:21]=[C:22]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:23][NH:24][CH2:25]CCO>>[F:35][C:32]([F:34])([F:33])[C:30]1[CH:29]=[C:22]([CH:21]=[C:20]([C:19]([F:37])([F:36])[F:18])[CH:31]=1)[CH2:23][NH:24][CH2:25][CH2:8][OH:9]Participants
Procedure
2-Chloro-5-methyl-4-phenyl-3-pyridinecarboxylic acid was used in place of 2-chloro-4-phenyl-3-pyridinecarboxylic acid in Step 2 in Reference Example 12, reacted with N-[3,5-bis(trifluoromethyl)benzyl]-N-(3-hydroxypropyl)amine that had been obtained in Step 1 in Reference Example 23, in place of N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-hydroxyethyl)amine, and treated in the same manner as in Step 2 in Reference Example 12, to obtain the entitled compound as a pale yellow oil. NMR(200 MHz, CDCl3) ppm: 1.10-1.80(2H,m), 2.06(3H×1/2,s), 2.08(3H×1/2,s), 2.80-3.30(3H,m), 3.35-3.70(1H,m), 4.08(1H×1/2,d,J=16.4 Hz), 4.39(1H×1/2,d,J=15.0 Hz), 4.47(1H×1/2,d,J=16.4 Hz), 4.70(1H×1/2,d,J=15.0 Hz), 6.90-7.62(7H,m), 7.72(1H×1/2,s), 7.77(1H×1/2,s), 8.28(1H×1/2,s), 8.31(1H×1/2,s).
Sources & evidence
- ORD record
- ord-95788070076048aa9f08ea32bad20dd7
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05786352
Reaction notes
Loading…