Benzene, (2-bromoethoxy)- → (1R,3R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromide

HRID 551385Notes

Reaction equation

HRID 551385 reaction equation
CN1CCC[C@@H](OC(=O)C(O)(C2SC=CC=2)C2SC=CC=2)C1.O(CC[Br:32])C1C=CC=CC=1.[Br-].[OH:34][C:35]([C:60]1[S:61][CH:62]=[CH:63][CH:64]=1)([C:55]1[S:56][CH:57]=[CH:58][CH:59]=1)[C:36]([O:38][C@@H:39]1[CH2:44][CH2:43][CH2:42][N+:41]([CH3:54])([CH2:45][CH2:46][O:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:40]1)=[O:37]>C(#N)C>[Br-:32].[OH:34][C:35]([C:55]1[S:56][CH:57]=[CH:58][CH:59]=1)([C:60]1[S:61][CH:62]=[CH:63][CH:64]=1)[C:36]([O:38][C@@H:39]1[CH2:44][CH2:43][CH2:42][N@+:41]([CH3:54])([CH2:45][CH2:46][O:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:40]1)=[O:37]

Participants

5

Reactant 3

HCID 68526Benzene, (2-bromoethoxy)-HCID 67196562(1r/s,3r)-3-(2-Hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromideHCID 67199874Hydroxy-di-thiophen-2-yl-acetic acid (R)-1-methyl-piperidin-3-yl ester

Product 1

HCID 67196564(1R,3R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Hydroxy-di-thiophen-2-yl-acetic acid (R)-1-methyl-piperidin-3-yl ester (0.57, 0.00169 mol) is dissolved in acetonitrile (3 ml) at 60° C. and 2-phenoxyethyl bromide (0.51 g, 0.00254 mol) in Acetonitrile (1 ml) is added dropwise. The reaction mixture is refluxed for 96 hours, cooled to room temperature and left in the refrigerator. This gives an approximately 1:1 mixture of isomers (1R/S,3R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromide (97a). The suspension is filtered off and washed with cold acetonitrile to yield (1R,3R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromide (97b) as a white solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 96 hours
  2. waitleft in the refrigerator
  3. customThis gives
  4. filtrationThe suspension is filtered off
  5. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-34b5ebe82da3425f90bd27095ca0d86d
Source dataset
uspto-grants-2011_05
Patent number
US07947730B2

Reaction notes

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