Hydrochloric Acid → HCID 15337638, compound

HRID 1016498Notes

Reaction equation

HRID 1016498 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 184070691,1-Dimethylethyl 4-(5-cyano-1H-indol-3-yl)-1-piperidinecarboxylate

Product 1

HCID 15337638HCID 15337638, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 3-[1-(t-butoxycarbonyl)-4-piperidyl]-5-cyanoindole (8.4 g, 25.8 mmol) in methanol (260 mL) was treated with 4N hydrochloric acid in dioxane (64 mL, 256 mmol). After stirring at ambient temperature for 2 hours, the solution was concentrated. The residue was neutralized with 1N NaOH, extracted with ethyl acetate, dried, and concentrated to afford the product as a white solid (5.29 g, 91%). 1H-NMR δ(CDCl3) 8.59 (br s, 1 H), 8.00 (s, 1 H), 7.40 (s, 2 H), 7.09 (s, 1 H), 3.23 (br d, 1 H), 2.93 (m, 1 H), 2.81 (br t, 2 H), 2.01 (m, 2 H), 1.66 (m, 4 H).

Workup

  1. concentrationthe solution was concentrated
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c1a04c773e994d6f8015f959e44ab92c
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

Loading…