Sodium Hydroxide → 4-((4-((((trans)-2-(4-Cyclopropylphenyl)cyclopropyl)amino)methyl)piperidin-1-yl)methyl)benzoic acid

HRID 529369Notes

Reaction equation

HRID 529369 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([C@@H:10]3[CH2:12][C@H:11]3[NH:13][CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C@@H:10]3[CH2:12][C@H:11]3[NH:13][CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=4)[CH2:17][CH2:16]3)=[CH:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68391792Methyl 4-((4-((((trans)-2-(4-cyclopropylphenyl)cyclopropyl)amino)methyl)piperidin-1-yl)methyl)benzoate

Product 1

HCID 665715924-((4-((((trans)-2-(4-Cyclopropylphenyl)cyclopropyl)amino)methyl)piperidin-1-yl)methyl)benzoic acidYield 40.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-((4-(((trans-2-(4-cyclopropylphenyl)cyclopropyl)amino)methyl)piperidin-1-yl)methyl)benzoate (118 mg, 0.282 mmol) in methanol (3 mL) was added sodium hydroxide (1M, 2 mL, 2 mmol), and the mixture was stirred at room temperature for 6 h. The mixture was purified using reverse-phase HPLC. The fractions containing the product were combined, treated with 1N HCl and concentrated. The residue was dried under vacuum to give 46 mg of product (HCl salt) as white solid. MS: (M+H)+=405.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.54-0.72 (m, 2H), 0.84-1.01 (m, 2H), 1.15-1.29 (m, 1H), 1.51-1.71 (m, 3H), 1.82-2.12 (m, 4H), 2.96 (br. s., 4H), 3.12 (br. s., 1H), 4.33 (br. s., 2H), 6.94-7.14 (m, 4H), 7.74 (d, J=8.08 Hz, 2H), 8.01 (d, J=8.34 Hz, 2H).

Workup

  1. customThe mixture was purified
  2. additionThe fractions containing the product
  3. additiontreated with 1N HCl
  4. concentrationconcentrated
  5. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-4d193828d3e9456199046c6fcc1fafc2
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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