2-Methylpiperidine → HCID 59772989, compound

HRID 2220700Notes

Reaction equation

HRID 2220700 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH:2]=1.[CH3:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][CH2:8][CH2:9][C:10]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH:20]2[CH3:19])=[O:12])[CH:2]=1

Participants

6

Reactant 4

HCID 79742-MethylpiperidineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59773025HCID 59773025, compound

Product 1

HCID 59772989HCID 59772989, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the 3-(biphenyl-3-ylamino)-propionic acid 1.6 g (6.6 mmol), 2-methylpiperidine 0.78 g (7.9 mmol), was added the solid O-(benzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate 4.7 g (1.3 mmol), and triethylamine 3.86 mL (27 mmol) in 25 mL of dichloromethane and left overnight at room temperature. The reaction mixture was washed with water, the organic layer, dried over magnesium sulfate, filtered, and concentrated under vacuum. The compound was purified using silica gel chromatography and was eluted with ethyl acetate, yield to 2 g material.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer, dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe compound was purified
  6. washwas eluted with ethyl acetate

Sources & evidence

ORD record
ord-e6197f262e384a73b279045f4b16a692
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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