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

HRID 1174710Notes

Reaction equation

HRID 1174710 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-8b31b2e9afb94ee8a26a675fb50bff76
Source dataset
uspto-grants-2010_11
Patent number
US07838547B2

Reaction notes

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