(R)-(-)-2-Amino-1-propanol → (R)-2-Chloro-5-[2-(2-hydroxy-1-methylethylamino)ethoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, hydrochloride

HRID 2085646Notes

Reaction equation

HRID 2085646 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24]Cl)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[NH2:26][C@H:27]([CH3:30])[CH2:28][OH:29]>>[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][NH:26][C@H:27]([CH3:30])[CH2:28][OH:29])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 227314842-chloro-5-(2-chloroethoxy)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 10115285(R)-2-Chloro-5-[2-(2-hydroxy-1-methylethylamino)ethoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, hydrochloride

Procedure

Prepared according to the method of Example 4 using 2-chloro-5-(2-chloroethoxy)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 11a, 0.17 g) and (R)-2-amino-1-propanol (0.11 ml). The reaction mixture was partitioned between ethyl acetate and sodium hydrogencarbonate solution, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by RPHPLC (eluting with 25-95% MeCN in 0.1% AcONH4 aqueous) to give the title compound as the acetate salt. This was converted to the hydrochloride salt by stirring with 4M HCl in dioxane and concentrated under reduced pressure. Trituration with diethyl ether gave the title compound as a solid (0.05 g).

Workup

  1. customPrepared
  2. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogencarbonate solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by RPHPLC (eluting with 25-95% MeCN in 0.1% AcONH4 aqueous)

Sources & evidence

ORD record
ord-0270ff5ff24c419dace2bd4924fcdfb1
Source dataset
uspto-grants-2004_04
Patent number
US06720452B2

Reaction notes

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