Dimethyl Sulfoxide → (3S)-N-(4-oxocyclohexyl)-1-phenylpiperidine-3-carboxamide

HRID 656343Notes

Reaction equation

HRID 656343 reaction equation
Cl.N1CCC[C@H](C(OCC)=O)C1.BrC1C=CC=CC=1.[CH3:20][C:21](C)([O-:23])[CH3:22].[K+].CS(C)=O.[C:30]1([N:36]2[CH2:41][CH2:40][CH2:39][C@H:38]([C:42]([OH:44])=O)[CH2:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.F[P-](F)(F)(F)(F)F.[N:52]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:56]2[CH:57]=CC=C[C:55]=2N=N1>>[O:23]=[C:21]1[CH2:22][CH2:57][CH:56]([NH:52][C:42]([C@H:38]2[CH2:39][CH2:40][CH2:41][N:36]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:37]2)=[O:44])[CH2:55][CH2:20]1

Participants

7

Reactant 6

HCID 679Dimethyl SulfoxideHCID 7961BromobenzeneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23665647Potassium tert-butoxideHCID 45074034(S)-Ethyl piperidine-3-carboxylate hydrochlorideHCID 66743624(S)-1-Phenylpiperidine-3-carboxylic acid

Product 1

HCID 11688042(3S)-N-(4-oxocyclohexyl)-1-phenylpiperidine-3-carboxamide

Procedure

A solution of ethyl (3S)-piperidine-3-carboxylate hydrochloride (0.1 g, 0.0005 mol), bromobenzene (0.16 g, 0.0010 mol) and potassium tert-butoxide (0.12 g, 0.0010 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) was heated at 200° C. for 10 min. under microwave irradiation. The crude (3S)-1-phenylpiperidine-3-carboxylic acid was subjected to BOP-mediated coupling by using a procedure that was analogous to that described for the synthesis of example 129, step 3. LCMS: m/z 301.2 (M+H)+.

Workup

  1. customthat described for the synthesis of example 129, step 3

Sources & evidence

ORD record
ord-eca37b3f9f8e4189a14085bb5fb2d5d3
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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