Amantadine → (3S)-N-1-Adamantyl-1-phenylpiperidine-3-carboxamide

HRID 656337Notes

Reaction equation

HRID 656337 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6]O[CH2:4][CH2:3]1.[C:8]1(N2CCC[C@H](C(O)=O)C2)[CH:13]=[CH:12]C=[CH:10][CH:9]=1.[C:23]12([NH2:33])[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:77]=2N=N1.CN(C)[CH:96]=[O:97]>>[C:23]12([NH:33][C:96]([C@H:6]3[CH2:77][CH2:4][CH2:3][N:2]([C:1]4[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=4)[CH2:7]3)=[O:97])[CH2:30][CH:29]3[CH2:28][CH:27]([CH2:26][CH:25]([CH2:31]3)[CH2:24]1)[CH2:32]2

Participants

7

Reactant 6

HCID 2130AmantadineHCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2724699PyBOPHCID 66743624(S)-1-Phenylpiperidine-3-carboxylic acid

Product 1

HCID 11702835(3S)-N-1-Adamantyl-1-phenylpiperidine-3-carboxamide

Procedure

4-Methylmorpholine (43 μL, 0.00039 mol) was added to a mixture of (3S)-1-phenylpiperidine-3-carboxylic acid (20 mg, 0.0001 mol), tricyclo[3.3.1.13,7]decane-1-amine (18 mg, 0.00012 mol), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (53.2 mg, 0.000102 mol) or benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (45.2 mg, 0.000102 mol) in N,N-dimethylformamide (0.5 mL, 0.006 mol). The reaction mixture was stirred at rt for 2 hrs and the crude reaction mixture was purified by prep-LCMS to afford the desired product. LCMS: m/z 339.3 (M+H)+.

Workup

  1. customthe crude reaction mixture
  2. customwas purified by prep-LCMS

Sources & evidence

ORD record
ord-ccd35c2225544ef1b0e94ce23e6b88c8
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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