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Triethylamine → (2S)-1-azido-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol

HRID 2233374
Notes
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Reaction equation

HRID 2233374 reaction equation
[N+](C1C=C(S(O[CH2:14][C@H:15]2[CH2:17][O:16]2)(=O)=O)C=CC=1)([O-])=O.C(N(CC)CC)C.[Cl:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][C:38]=1[Cl:39])[O:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[N-:40]=[N+:41]=[N-:42].[Na+]>CN(C=O)C>[N:40]([CH2:17][C@@H:15]([OH:16])[CH2:14][N:33]1[CH2:34][CH2:35][CH:30]([O:29][C:28]2[CH:36]=[CH:37][C:38]([Cl:39])=[C:26]([Cl:25])[CH:27]=2)[CH2:31][CH2:32]1)=[N+:41]=[N-:42]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 37320424-(3,4-Dichlorophenoxy)piperidine

Product 1

HCID 59295965(2S)-1-azido-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

(2R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate (21.1 g, 81.3 mmol) in DMF (300 ml) was treated with triethylamine (22.6 ml, 163.0 mmol) followed by 4-(3,4-dichlorophenoxy)-piperidine (20 g, 81.3 mmol). The mixture was stirred overnight at 60° C. Sodium azide (16 g, 243.9 mmol) was added to the mixture and the reaction was stirred for a further 72 h. The solution was carefully concentrated under vacuum and the residue was diluted with water (600 ml), extracted with ethyl acetate (1500 ml). The organic layer was washed twice with water (500 ml), then brine (200 ml) and concentrated under vacuum to afford an oil.

Workup

  1. stirringthe reaction was stirred for a further 72 h
  2. concentrationThe solution was carefully concentrated under vacuum
  3. additionthe residue was diluted with water (600 ml)
  4. extractionextracted with ethyl acetate (1500 ml)
  5. washThe organic layer was washed twice with water (500 ml)
  6. concentrationbrine (200 ml) and concentrated under vacuum
  7. customto afford an oil

Sources & evidence

ORD record
ord-50c0131af8e84877ba9f5c46efbe54e8
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709500B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes