Ethanolamine → N-[4-(4-Acetyl-1-oxa-4,7-diazaspiro[4,4]non-7-yl)phenyl]-4-butoxybenzamide

HRID 2043095Notes

Reaction equation

HRID 2043095 reaction equation
[CH2:1]([O:5][C:6]1[CH:26]=[CH:25][C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][CH2:22][C:21](=[O:24])[CH2:20]3)=[CH:15][CH:14]=2)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:27]([CH2:29][NH2:30])O.C(=O)([O-])[O-].[K+].[K+].[C:37](Cl)(=[O:39])[CH3:38]>ClCCl>[C:37]([N:30]1[C:21]2([CH2:22][CH2:23][N:19]([C:16]3[CH:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[C:9]4[CH:25]=[CH:26][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=4)=[CH:14][CH:15]=3)[CH2:20]2)[O:24][CH2:27][CH2:29]1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 21105481HCID 21105481, compound

Product 1

HCID 59558092N-[4-(4-Acetyl-1-oxa-4,7-diazaspiro[4,4]non-7-yl)phenyl]-4-butoxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-butoxy-N-[4-(3-oxopyrrolidin-1-yl)phenyl]benzamide (70 mg), ethanolamine (12 mg), potassium carbonate (27 mg) and dichloromethane (3 ml) was stirred for 48 hours, and then acetyl chloride (16 mg) was added. After 20 hours, the mixture was diluted with dichloromethane, washed with water, dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 437.54 (C25H31N3O4); MS (ESI): 438 (M+H+) was obtained in this way.

Workup

  1. waitAfter 20 hours
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customMS (ESI): 438 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-597ce4032acf40d3a7a946559e853a1d
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

Loading…