Piperidine → HCID 53256742, compound

HRID 854231Notes

Reaction equation

HRID 854231 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.F[B-](F)(F)F.[N:20]1(OC(N(C)C)=[N+](C)C)[C:24]2C=[CH:26][CH:27]=[CH:28][C:23]=2N=N1.C(N(C(C)C)C(C)C)C.N1CCCCC1>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([N:20]1[CH2:26][CH2:27][CH2:28][CH2:23][CH2:24]1)=[O:14])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 855576-Hydroxy-2-naphthoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 53256742HCID 53256742, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g (0.003 mol) 6-hydroxy-2-naphtoic acid, 1.2 g (0.003 mol) 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, 2.3 ml (0.013 mol) N-ethyldiisopropylamine and 0.29 ml (0.030 mol) piperidine in 10 ml DMF was stirred for 16 h at room temperature. The mixture was concentrated to dryness and 50 ml ethyl acetate, 30 ml water and 20 ml NaHCO3 aq. (10%) was added. The aqueous phase was extracted with 50 ml ethyl acetate and the combined organic layers were purified with column chromatography on silica. The product fractions were concentrated to dryness and titurated twice with 20 ml diethyl ether/heptane 1/1. The residue was dried under vacuum at 50° C. to yield 0.58 g (0.0227 mmol; 85%) of the title compound as light brown solid. MS (m/e): 254.3 (MH−, 100%)

Workup

  1. concentrationThe mixture was concentrated to dryness and 50 ml ethyl acetate, 30 ml water and 20 ml NaHCO3 aq. (10%)
  2. additionwas added
  3. extractionThe aqueous phase was extracted with 50 ml ethyl acetate
  4. customthe combined organic layers were purified with column chromatography on silica
  5. concentrationThe product fractions were concentrated to dryness
  6. customThe residue was dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-40870d7a2cd141509540390127c2bb3b
Source dataset
uspto-grants-2007_08
Patent number
US07259158B2

Reaction notes

Loading…