3,4-Dichlorophenylacetic acid → 2-(3,4-Dichlorophenylacetyl)-2,5-diazabicyclo[4.0.4]decane

HRID 430936Notes

Reaction equation

[CH:1]12[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[NH:5][CH2:4][CH2:3][NH:2]2.[Cl:11][C:12]1[CH:13]=[C:14]([CH2:19][C:20](O)=[O:21])[CH:15]=[CH:16][C:17]=1[Cl:18]>>[Cl:11][C:12]1[CH:13]=[C:14]([CH2:19][C:20]([N:2]2[CH2:3][CH2:4][NH:5][CH:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH:1]23)=[O:21])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

Reactant 2

HCID 798743,4-Dichlorophenylacetic acid

HCID 17906435Decahydroquinoxaline

Product 1

HCID 155417542-(3,4-Dichlorophenylacetyl)-2,5-diazabicyclo[4.0.4]decane

Procedure

The title compound of Example 15 base (0.49 g, 3.5 mmol) was coupled with 3,4-dichlorophenylacetic acid (1.07 g, 5.2 mmol) as described in Example 5 to give the amide as a crystalline solid: mp 119-120° C. (2-propanol); 1H-NMR (CDCl3) σ 7.39 (d, J=8.3 Hz, 1H), 7.35 (d, J=2.0 Hz, 1H), 7.09 (d, J=8.3 Hz, 1H), 4.48 (m, 1H), 3.66 (br s, 2H), 3.64 (m, 1H), 3.29 and 2.87 (m, 1H), 2.64-2.85 (complex m, 2H), 2.41 and 2.09 (m, 1H), 1.93-2.06 (complex m, 2H), 1.40-1.87 (complex m, 5H), 1.12-1.36 (complex m, 2H); Anal (calcd for C16H20Cl2N2O): C 58.72, H 6.16, N 8.56. Found: C 58.80, H 6.17, N 8.52.

Sources & evidence

ORD record: ord-8c1322bd62bb4b2f99630c6f2184b478
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06656930B2

Reaction notes

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