Diisopropylethylamine → HCID 46849923, compound

HRID 2177530Notes

Reaction equation

HRID 2177530 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]([NH2:14])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.C(N(C(C)C)C(C)C)C.[CH3:24][O:25][C:26]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[C:27]=1[C:28](Cl)=[O:29]>ClCCl>[CH3:24][O:25][C:26]1[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[C:31]([C:39]([F:40])([F:41])[F:42])[C:27]=1[C:28]([NH:14][C:4]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:6][CH2:7][N:2]([CH3:1])[CH2:3]1)=[O:29]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 179993452-Methoxy-4,6-bis(trifluoromethyl)benzoyl chlorideHCID 59438412HCID 59438412, compound

Product 1

HCID 46849923HCID 46849923, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 205 mg (1.077 mmol) rac-1-methyl-3-phenyl-piperidin-3-ylamine (Example A.1) and 369 ul (2.154 mmol) N-ethyldiisopropylamine in dichloromethane (2.5 ml) was added dropwise a solution of 430 mg (1.4 mmol) 2-methoxy-4,6-bis-trifluoromethyl-benzoyl chloride (CAS: 886503-47-5) in dichloromethane (2.0 ml) at room temperature. The mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 340 mg (69%) of the title compound as a light yellow foam. MS (m/e): MS (m/e): 461.4 (M+H).

Workup

  1. customat room temperature
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-3f78d4167c79449885adf6f1b74f5d9c
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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