Isopropylamine → 2-Chloro-5-[3-[(1-methylethyl)amino]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, hydrochloride salt

HRID 1816046Notes

Reaction equation

HRID 1816046 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[Cl:5][C:6]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28]OS(C)(=O)=O)=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9]>O1CCCC1>[ClH:5].[Cl:5][C:6]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][NH:4][CH:1]([CH3:3])[CH3:2])=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 12988688chloro-5-[3-[(methylsulfonyl)oxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 102969402-Chloro-5-[3-[(1-methylethyl)amino]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, hydrochloride salt

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Isopropylamine (0.5 ml) was added to a solution of 2-chloro-5-[3-[(methylsulfonyl)oxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.250 g, Example 6e) in tetrahydrofuran (20 ml) and heated at 70° C. in a sealed tube for 24 h. The mixture was concentrated under reduced pressure and the residue purified by solid phase extraction on SCX resin. The title product was isolated as the hydrochloric acid salt (0.10 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue purified by solid phase extraction on SCX resin

Sources & evidence

ORD record
ord-61a9f7fa963a4a6e9166de50a2f18bbe
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

Loading…