3-Bromo-1-propanol → [3-(6-Chloro-pyridin-2-yloxy)-propyl]-(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amine hydrochloride salt

HRID 902649Notes

Reaction equation

HRID 902649 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.[C:9]1([CH:15]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:16][N:17]([CH2:30][CH2:31][CH2:32]O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[C:20]=2[Cl:29])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.OC1C=C(C=CC=1)CC1N(COCC)N=NN=1.BrCCCO.Cl.C(OCC)C>C(OCC)C>[ClH:1].[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH2:32][CH2:31][CH2:30][N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[C:20]=2[Cl:29])[CH2:16][CH:15]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 123083-Bromo-1-propanolHCID 10953452Ether hydrochlorideHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-olHCID 688254685-(3-Hydroxy-benzyl)-ethoxymethyl-1,2,3,4-tetrazoleHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 86598285[3-(6-Chloro-pyridin-2-yloxy)-propyl]-(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amine hydrochloride saltYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the procedure of Example 6(d), except 6-chloro-2-pyridinol (Aldrich) and N-(2,2-Diphenylethyl)-N-(3-hydroxy-propyl)-N-(2-chloro-3-trifluoromethyl-benzyl)amine were used instead of 5-(3-hydroxy-benzyl)-ethoxymethyl-1,2,3,4-tetrazole and 3-bromo-propanol in step 6(d), the title compound was synthesized as the free base. The tertiaryamine was then dissolved in diethyl ether and acidified with 1.0 M HCl/diethyl ether to give 90 mg (32% yield) of the title compound as a white solid. MS (ESI) 559.0 (M+).

Workup

  1. customthe title compound was synthesized as the free base

Sources & evidence

ORD record
ord-bf256deee0f6453580785b366ab315b9
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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