tert-Butyl (3-hydroxypropyl)methylcarbamate → 2-Chloro-5-[3-[3-(methylamino)propoxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide, dihydrochloride salt

HRID 719653Notes

Reaction equation

HRID 719653 reaction equation
CC(OC(=O)[N:7]([CH2:9][CH2:10][CH2:11][OH:12])[CH3:8])(C)C.[Cl:14][C:15]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37]I)=[CH:31][C:16]=1[C:17]([NH:19][CH2:20][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2)=[O:18]>ClCCl.FC(F)(F)C([O-])=O.[Ag+]>[ClH:14].[ClH:14].[Cl:14][C:15]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37][O:12][CH2:11][CH2:10][CH2:9][NH:7][CH3:8])=[CH:31][C:16]=1[C:17]([NH:19][CH2:20][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2)=[O:18]

Participants

5

Reactant 2

HCID 10375241tert-Butyl (3-hydroxypropyl)methylcarbamateHCID 689262302-Chloro-5-(3-iodopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

Product 1

HCID 101181242-Chloro-5-[3-[3-(methylamino)propoxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide, dihydrochloride saltYield 7.3%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Silver trifluoroacetate (0.7 g, 3.2 mmol) was added to 1,1-dimethylethyl (3-hydroxypropyl)methyl carbamic acid (1.8 g, 9.5 mmol), [Synth. Commun. (1995), 25(14), 2135–43] in dichloromethane (20 ml). After 10 min. 2-chloro-5-(3-iodopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl) benzamide (1.0 g, Example 70a) was added and the mixture was stirred for 24 h The resulting mixture was washed with water and concentrated. Treatment with 4M hydrochloric acid in 1,4-dioxane/methanol, concentration and purification by RPHPLC gave the title compound (26 mg) as a white solid.

Workup

  1. washwas washed with water
  2. concentrationconcentrated
  3. concentrationTreatment with 4M hydrochloric acid in 1,4-dioxane/methanol, concentration and purification by RPHPLC

Sources & evidence

ORD record
ord-3dd95ca2e752426eb491dbe5879f154a
Source dataset
uspto-grants-2006_11
Patent number
US07132457B2

Reaction notes

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