Methanol → HCID 67384766, compound

HRID 2360985Notes

Reaction equation

HRID 2360985 reaction equation
C[O:2][C:3]([C:5]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].C[OH:28].[OH-].[Na+]>O1CCCC1>[C:14]([O:13][C:11]([N:8]1[CH2:7][CH2:6][C:5]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:28])[NH2:26])=[CH:21][CH:20]=2)([C:3]([OH:2])=[O:4])[CH2:10][CH2:9]1)=[O:12])([CH3:16])([CH3:15])[CH3:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67385030HCID 67385030, compound

Product 1

HCID 67384766HCID 67384766, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-cyanobenzyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (23.04 mmol; 8.26 g) (prepared as in Example 1, but substituting 4-cyanobenzylbromide for 4-biphenylmethyl bromide), in tetrahydrofuran (50 mL) and methanol (50 mL) was added an aqueous 1M NaOH solution (46.1 mmol; 46.1 mL), and the resulting solution was heated to reflux for 48 hours. The mixture was then evaporated and an aqueous 1N HCl solution (50 mL) was added, resulting in the formation of a precipitate. The solid was separated via filtration and dried under vacuum to yield 4-(4-carbamoylbenzyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester. MS (ESI) m/z 384.89 [M+Na]+.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 48 hours
  3. customThe mixture was then evaporated
  4. additionan aqueous 1N HCl solution (50 mL) was added
  5. customresulting in the formation of a precipitate
  6. customThe solid was separated via filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-62f1406263594513b635bf653407dbb7
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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