Sodium Hydroxide → 1-(2-ethoxy-ethyl)-3-(1-{3-[4-(2H-tetrazol-5-yl)-phenoxy]-propyl}-piperidin-4-yl)-1H-indole

HRID 1840970Notes

Reaction equation

HRID 1840970 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=3)[CH2:17][CH2:16]2)=[CH:7]1)[CH3:2].[Cl-].[NH4+].[N-:35]=[N+:36]=[N-:37].[Na+].[OH-].[Na+]>CN(C=O)C>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][C:28]([C:29]4[N:35]=[N:36][NH:37][N:30]=4)=[CH:31][CH:32]=3)[CH2:19][CH2:20]2)=[CH:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23444823HCID 23444823, compound

Product 1

HCID 179286201-(2-ethoxy-ethyl)-3-(1-{3-[4-(2H-tetrazol-5-yl)-phenoxy]-propyl}-piperidin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.108 g (0.25 mmol) of 4-(3-{4-[l-(2-ethoxyethyl)-1H-indol-3-yl]-piperidin-1-yl}-propoxy)-benzonitrile in 1.5 mL of anhydrous DMF, 0.110 g (2 mmol) of ammonium chloride and 0.135 g (2 mmol) of sodium azide were added. The crude mixture was heated at 110° C. for 18 hours and after cooling at room temperature, 1 mL of an aqueous solution of 2N sodium hydroxide was added. The mixture was taken to pH=6 and the aqueous phase was extracted with ethyl acetate. After purification by flash cromatography over silica gel 0.05 g (41% yield) of the desired product were obtained.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate

Sources & evidence

ORD record
ord-bcc75cd6595e4e97b6305974d74fdb45
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

Loading…