Citric Acid → HCID 178445765, compound

HRID 525451Notes

Reaction equation

HRID 525451 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:22]=O)[CH:18]=3)[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]1.C(O)C.C([BH3-])#N.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:22][N:24]4[CH2:29][CH2:28][CH:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]4)[CH:18]=3)[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 311Citric AcidHCID 702EthanolHCID 37734-Piperidinecarboxylic acidHCID 5003444Sodium cyanoborohydrideHCID 866684172-(4-Tert-butyl-cyclohexyloxy)-quinoline-6-carbaldehyde

Product 1

HCID 178445765HCID 178445765, compoundYield 16%

Procedure

To the solution of 2-(4-tert-butyl-cyclohexyloxy)-quinoline-6-carbaldehyde (350 mg, 1.1 mmol) and piperidine-4-carboxylic acid (145 mg, 1.12 mmol) in ethanol (8 mL, 100 mmol) was heated to reflux for 2 h. The yellow solution was cooled to rt and sodium cyanoborohydride (84.8 mg, 1.35 mmol) was added and was heated to reflux for 1 h. After cooled down to rt, citric acid was added and concentrated down. The solid was suspended in water and filtrate, and the collected solid was washed thoroughly with water. HPLC purification of the solid gives the product. 77 mg, yield: 16%. ESI-MS (M+1)+: 425.00.

Workup

  1. temperatureto reflux for 2 h
  2. temperaturewas heated
  3. temperatureto reflux for 1 h
  4. temperatureAfter cooled down to rt
  5. concentrationconcentrated down
  6. washfiltrate, and the collected solid was washed thoroughly with water
  7. customHPLC purification of the solid
  8. customgives the product

Sources & evidence

ORD record
ord-dd87ff43f80343518822a72fd3858dd6
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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