1-Benzyl-4-piperidone → HCID 59809531, compound

HRID 2114514Notes

Reaction equation

HRID 2114514 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[OH:11].NC1C=CC(C#N)=CC=1OC1C=CC=CC=1Br.[CH2:30]([N:37]1[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OC(N1CCC(=O)CC1)=O)(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH:40]2[CH2:39][CH2:38][N:37]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:42][CH2:41]2)[C:5]=1[OH:11]

Participants

7

Reactant 6

HCID 192201-Benzyl-4-piperidoneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 12782444Methyl 3-amino-2-hydroxybenzoateHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 59809535HCID 59809535, compound2×

Product 1

HCID 59809531HCID 59809531, compound

Procedure

Using an adaptation of the method described in Procedure 3, substituting 3-amino-2-hydroxybenzoic acid methyl ester, 1l for 4-amino-3-(2-bromophenoxy)-benzonitrile, 2a, 1-benzylpiperidin-4-one for 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, and tetramethylammonium triacetoxyborohydride for sodium triacetoxyborohydride, the title compound 3-(1-benzylpiperidin-4-ylamino)-2-hydroxybenzoic acid methyl ester, 2l was obtained.

Sources & evidence

ORD record
ord-52f8aacb05cf451598384a4c7f805d5c
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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