Triethylamine → HCID 59305204, compound

HRID 1971142Notes

Reaction equation

HRID 1971142 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[F:9][C:10]1[CH:11]=[C:12]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH:13]=[CH:14][C:15](O)=[O:16].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>ClCCl>[F:9][C:10]1[CH:11]=[C:12](/[CH:13]=[CH:14]/[C:15]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)=[O:16])[CH:18]=[C:19]([F:21])[CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4207714-PiperidinemethanolHCID 5228103-(3,5-Difluorophenyl)acrylic acid

Product 1

HCID 59305204HCID 59305204, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Piperidinemethanol (17.7 g, 1.0 eq.), 3,5-difluorocinnamic acid (28.3 g, 1.0 eq.) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP, 78.2 g, 1.15 eq.) were dissolved in dichloromethane (DCM, 700 mL). Triethylamine (TEA, 46.6 g, 3.0 eq.) was added and the resulting solution was stirred at room temperature overnight. LCMS showed 100% conversion. The reaction mixture was concentrated and purified via silica gel column eluting with 0-75% ethyl acetate in hexanes to afford the product as a white solid (35 g, 81%). MS (ES) m/e 282 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified via silica gel column
  3. washeluting with 0-75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b4c13832db254d739d2275280b664c88
Source dataset
uspto-grants-2013_04
Patent number
US08431590B2

Reaction notes

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