3-Phenylbenzaldehyde → 1-([1,1'-Biphenyl]-3-ylmethyl)-6-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperidin-2-one

HRID 594654Notes

Reaction equation

HRID 594654 reaction equation
[NH2:1][CH:2]([C:10]1[C:19]2[O:18][CH2:17][CH2:16][O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8]C)=O.[C:20]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]=O)[CH:21]=1>>[C:20]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][N:1]2[CH:2]([C:10]3[C:19]4[O:18][CH2:17][CH2:16][O:15][C:14]=4[CH:13]=[CH:12][CH:11]=3)[CH2:3][CH2:4][CH2:5][C:6]2=[O:8])[CH:21]=1

Participants

3

Reactant 2

HCID 1210533-PhenylbenzaldehydeHCID 69095861Methyl 5-amino-5-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pentanoate

Product 1

HCID 690819341-([1,1'-Biphenyl]-3-ylmethyl)-6-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperidin-2-one

Procedure

Prepared according to the described general procedure 1 (GP1) by reaction of methyl 5-amino-5-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pentanoate with commercially available [1,1′-biphenyl]-3-carbaldehyde. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.91 min.; [M+H]+: 400.01 g/mol.

Workup

  1. customPrepared
  2. customSubsequent purification by preparative HPLC
  3. customafforded the target compound

Sources & evidence

ORD record
ord-ea9c722c3533448180892f394d65b09a
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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