Triethylamine → HCID 69076363, compound

HRID 1433172Notes

Reaction equation

HRID 1433172 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[OH:35][C:36]1([C@@H:42]([C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([O:52][C:53]([F:56])([F:55])[F:54])[CH:47]=2)[C:43]([OH:45])=O)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.[CH3:57][C@H:58]1[CH2:63][NH:62][CH2:61][C@@H:60]([CH3:64])[NH:59]1>C(Cl)Cl>[CH3:57][CH:58]1[NH:59][CH:60]([CH3:64])[CH2:61][N:62]([C:43](=[O:45])[C@@H:42]([C:36]2([OH:35])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]2)[C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([O:52][C:53]([F:56])([F:54])[F:55])[CH:47]=2)[CH2:63]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 16755457HCID 16755457, compound

Product 1

HCID 69076363HCID 69076363, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In one experiment, (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (41.73 g, 94.35 mmol) and triethylamine (88 mL, 630 mmol) were added to a mixture of (R)-2-(1-hydroxycyclohexyl)-2-(3-(trifluoromethoxy)phenyl)acetic acid (20.0 g, 62.9 mmol) and cis-2,6-dimethylpiperazine (7.17 g, 62.9 mmol) in methylene chloride (150 mL) at RT. After stirring for 18 h, the mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (50 to 100% ethyl acetate in heptane) to afford 1-(3,5-Dimethyl-piperazin-1-yl)-2-(R)-(1-hydroxy-cyclohexyl)-2-(3-trifluoromethoxy-phenyl)-ethanone (24.3 g, 93%).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (50 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-3ed4ba58c3be4ea89d914fcd4535a26c
Source dataset
uspto-grants-2009_11
Patent number
US07612210B2

Reaction notes

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