Formaldehyde → (cis)-4-{[1-(4-Chlorophenyl)-1H-tetrazol-5-yl]methyl}-2,6-dimethylmorpholine

HRID 517757

Reaction equation

HRID 517757 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[CH2:9]=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]#[C-:19])=[CH:14][CH:13]=1.C[Si]([N:24]=[N+:25]=[N-:26])(C)C>CO>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:19]([CH2:9][N:4]3[CH2:5][C@H:6]([CH3:8])[O:7][C@H:2]([CH3:1])[CH2:3]3)=[N:26][N:25]=[N:24]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 746704-Chlorophenyl isocyanideHCID 78378AzidotrimethylsilaneHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 86691886(cis)-4-{[1-(4-Chlorophenyl)-1H-tetrazol-5-yl]methyl}-2,6-dimethylmorpholine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (cis)-2,6-dimethylmorpholine (104 mg, 0.900 mmol, Alfa Aesar, Ward Hill, USA) in methanol (3 mL) was added formaldehyde (37% aqueous) (0.067 mL, 0.900 mmol). The reaction mixture was shaken at room temperature for 2 hours. To the reaction mixture was added 4-chlorophenyl isocyanide (138 mg, 1 mmol) and trimethylsilylazide (0.133 mL, 1.00 mmol). The reaction mixture was shaken at room temperature for a further 18 hours.

Workup

  1. stirringThe reaction mixture was shaken at room temperature for a further 18 hours

Sources & evidence

ORD record
ord-5ec900c6c37741e98fb497b74b02dcc7
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Linked notes

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