Triethylamine → HCID 68407751, compound

HRID 1916022Notes

Reaction equation

HRID 1916022 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([F:25])[CH2:23][CH:22]2[NH2:24])=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C@@:21]2([F:25])[CH2:23][C@H:22]2[NH:24][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[C:2]([F:13])([F:12])[F:1])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 44398212HCID 44398212, compound

Product 1

HCID 68407751HCID 68407751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-trifluoromethylbenzoyl chloride (0.10 g; 0.54 mmol) in dichloromethane (2 ml) added dropwise to a stirred solution of the amine from example P5 (compound Z1.004; 2-(4-chlorophenyl)-2-fluoro-cyclopropylamine; 0.100 g; 0.54 mmol) and triethylamine (0.15 ml; 1.08 m) in dichloromethane (3 ml). Stirred for 1 hr at room temperature then allowed to stand for 18 hr. The white precipitate was filtered off, washed with 2M HCl, saturated NaHCO3 and water and air dried giving the pure cis isomer. 0.065 g (34%).

Workup

  1. waitto stand for 18 hr
  2. filtrationThe white precipitate was filtered off
  3. washwashed with 2M HCl, saturated NaHCO3 and water and air
  4. customdried
  5. customgiving the pure cis isomer

Sources & evidence

ORD record
ord-f70d5a8add9d40ffa81ceb8eb089972e
Source dataset
uspto-grants-2013_12
Patent number
US08618023B2

Reaction notes

Loading…