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Sodium hydride → HCID 67024819, compound

HRID 254280
Notes
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Reaction equation

HRID 254280 reaction equation
O1[C:5]2([CH2:9][CH2:8][N:7]([C@H:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]3[O:16][CH2:17][C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[CH2:6]2)[O:4]CC1.[H-].[Na+].O1C2(CCN([C@H]3CCCC[C@@H]3O)C2)OCC1.ClC1C=CC=C(Cl)C=1CBr>COCCOC>[ClH:24].[O:4]=[C:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[O:16][CH2:17][C:18]2[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:25])[CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 16738222HCID 16738222, compoundHCID 86638599HCID 86638599, compound

Product 1

HCID 67024819HCID 67024819, compound

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent
3×

Procedure

(1R,2R)/(1S,2S)-2-[1,4-Dioxa-7-azaspiro[4.4]non-7-yl]-1-[(2,6-dichlorophenyl)methoxy]cyclohexane: To a suspension of sodium hydride, 80% oil dispersion (222 mg, 7.25 mmol) in ethyleneglycol dimethyl ether (20 mL) was added a solution of (1R,2R)/(1S,2S)-2-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)cyclohexanol (1.5 g, 6.60 mmol, step (v) of Example 15) in ethylene glycol dimethyl ether (10 mL). The resulting mixture was stirred at room temperature for 2 hours and then a solution of 2,6-dichlorobenzyl bromide (1.9 g, 7.9 mmol) in ethylene glycol dimethyl ether (10 mL) was added. The reaction mixture was refluxed for 16 hours under argon atmosphere, the solvent was evaporated in vacuo and the residue was taken up with water (70 mL). The aqueous solution was acidified to pH 0.5 with 6M HCl aqueous solution and then extracted with diethyl ether (2×40 mL). Basification of the aqueous solution to pH 4.5-5.5, followed by extraction with diethyl ether (4×40 mL), drying of the combined organic extracts over sodium sulfate and evaporation of the solvent in vacuo provided the intermediate title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours under argon atmosphere
  2. customthe solvent was evaporated in vacuo
  3. extractionextracted with diethyl ether (2×40 mL)
  4. extractionBasification of the aqueous solution to pH 4.5-5.5, followed by extraction with diethyl ether (4×40 mL)
  5. dry with materialdrying of the combined organic extracts over sodium sulfate and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-2eb99ebf396a402d970f797aa3580965
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07875611B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes