Dimethylformamide → (3RS,4RS)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-4-{4-[2-(4-(4,4,5,5,5-pentafluoropentyl)piperazino)ethyloxy]phenyl}thiochroman

HRID 1859349Notes

Reaction equation

HRID 1859349 reaction equation
[F:1][C:2]([F:16])([C:12]([F:15])([F:14])[F:13])[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.CN(C)C=O.Cl[CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[C:41]3[C:36](=[CH:37][C:38]([O:42][CH2:43][O:44][CH3:45])=[CH:39][CH:40]=3)[S:35][CH2:34][C:33]2([C:47]2[CH:52]=[CH:51][C:50]([O:53][CH2:54][O:55][CH3:56])=[CH:49][CH:48]=2)[CH3:46])=[CH:28][CH:27]=1>O>[CH3:45][O:44][CH2:43][O:42][C:38]1[CH:37]=[C:36]2[C:41]([CH:32]([C:29]3[CH:28]=[CH:27][C:26]([O:25][CH2:24][CH2:23][N:9]4[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:16])[C:12]([F:13])([F:14])[F:15])[CH2:11][CH2:10]4)=[CH:31][CH:30]=3)[C:33]([C:47]3[CH:52]=[CH:51][C:50]([O:53][CH2:54][O:55][CH3:56])=[CH:49][CH:48]=3)([CH3:46])[CH2:34][S:35]2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22123597(3RS,4RS)-4-[4-(2-chloroethyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-thiochromanHCID 221236141-(4,4,5,5,5-Pentafluoropentyl)piperazine

Product 1

HCID 22123602(3RS,4RS)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-4-{4-[2-(4-(4,4,5,5,5-pentafluoropentyl)piperazino)ethyloxy]phenyl}thiochromanYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Under argon atmosphere 4-(4,4,5,5,5-pentafluoropentyl)piperazine (70 mg, 0.4 mmol) was added to dimethylformamide solution (0.5 ml) of (3RS,4RS)-4-[4-(2-chloroethyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-thiochroman (69 mg, 0.13 mmol) and then stirred for 8 hours at 80° C. After adding water, the reaction solution was extracted with ethyl acetate. The extract was distilled under reduced pressure to remove the solvent and the crude product thus obtained was then purified using amino silica gel plate (ethyl acetate:hexane=1:2) to obtain 67 mg (yield: 77%) of the title compound.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. distillationThe extract was distilled under reduced pressure
  3. customto remove the solvent
  4. customthe crude product thus obtained
  5. customwas then purified

Sources & evidence

ORD record
ord-5e5e760e0ca2474ba89d8e414bfccd65
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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