Reaction #60725

ord-1610803d9b924dcd9e0249952dc4e700

Reaction equation

CC(C)N1CCC(COC[C@H](N)c2ccccc2)CC1
(R)-2-(1-isopropylpiperidin-4-ylmethoxy)-1-phenylethylamine
COc1ccc(C(=O)Cl)cc1
4-methoxybenzoyl chloride
→
COc1ccc(C(=O)N[C@@H](COCC2CCN(C(C)C)CC2)c2ccccc2)cc1.Cl
N-[(R)-2-(1-Isopropylpiperidine-4-ylmethoxy)-1-phenylethyl]-4-methoxybenzamide hydrochloride

Reactants

CC(C)N1CCC(COC[C@H](N)c2ccccc2)CC1
(R)-2-(1-isopropylpiperidin-4-ylmethoxy)-1-phenylethylamine
COc1ccc(C(=O)Cl)cc1
4-methoxybenzoyl chloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherafforded
  2. 2
    Otherafter purification (SiO2: 4:2:1 DCM:EtOAc:isopropyl-amine) and conversion to the HCl salt by general method A, 205 mg (91%) of the title compound

Procedure

Using coupling method B, (R)-2-(1-isopropylpiperidin-4-ylmethoxy)-1-phenylethylamine (150 mg, 0.54 mmol) and 4-methoxybenzoyl chloride (0.12 mL, 1.0 mmol) afforded, after purification (SiO2: 4:2:1 DCM:EtOAc:isopropyl-amine) and conversion to the HCl salt by general method A, 205 mg (91%) of the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07427632B2uspto-grants-2008_09