Diisopropylethylamine → HCID 178482921, compound

HRID 1047389Notes

Reaction equation

HRID 1047389 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17](O)=[O:18])[CH2:13][CH2:12]2)=[CH:6][C:5]=1[C:20]([F:23])([F:22])[F:21])([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.CN(C)C(ON1C2C=CC=CC=2N=N1)=[N+](C)C.[CH3:57][NH:58][CH2:59][CH:60]1[CH2:65][CH2:64][N:63]([C:66]2[CH:71]=[CH:70][C:69]([C:72]([F:75])([F:74])[F:73])=[CH:68][CH:67]=2)[CH2:62][CH2:61]1>ClCCl.CS(C)=O.C(#N)C>[CH3:57][N:58]([CH2:59][CH:60]1[CH2:65][CH2:64][N:63]([C:66]2[CH:67]=[CH:68][C:69]([C:72]([F:75])([F:73])[F:74])=[CH:70][CH:71]=2)[CH2:62][CH2:61]1)[C:17]([C@H:14]1[CH2:15][CH2:16][C@H:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:20]([F:21])([F:22])[F:23])[CH:6]=2)[CH2:12][CH2:13]1)=[O:18]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 62648464Methyl-[1-(4-trifluoromethyl-phenyl)-piperidin-4-ylmethyl]-amineHCID 178525754HCID 178525754, compound

Product 1

HCID 178482921HCID 178482921, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexanecarboxylic acid (7.88 g; 23.7 mmol, prepared in accordance with Example 42), diisopropylethyl amine (8.56 mL; 47.4 mmol), and tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (8.74 g; 22.6 mmol) in a mixture of dichloromethane (300 mL) and dimethylsulfoxide (5 mL) was stirred for 20 min. Afterward, methyl-[1-(4-trifluoromethyl-phenyl)-piperidin-4-ylmethyl]-amine (6.15 g; 22.6 mmol, prepared in accordance with Example 56) was added. The resulting suspension was stirred for 15.5 hr at room temperature. This resulted in a clear solution, which was extracted with water (1 L). The organic phase was dried over sodium sulfate. After concentrating under reduced pressure, the resulting residue obtained was dissolved in a small volume of acetonitrile and filtered over a silica gel pad. The solvent was removed under reduced pressure, and the resulting solid was dried at 40° C. under a pressure of 3 mbar to afford the desired product (12.9; 22.0 mmol).

Workup

  1. stirringThe resulting suspension was stirred for 15.5 hr at room temperature
  2. customThis resulted in a clear solution, which
  3. extractionwas extracted with water (1 L)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationAfter concentrating under reduced pressure
  6. customthe resulting residue obtained
  7. filtrationfiltered over a silica gel pad
  8. customThe solvent was removed under reduced pressure
  9. customthe resulting solid was dried at 40° C. under a pressure of 3 mbar

Sources & evidence

ORD record
ord-7b04e81889434352ad82c58416b17ca0
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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