Phthalic Anhydride → 3-(3'-Cyclopentyloxy-4'-methoxyphenyl)-3-phthalimido-1-propanol

HRID 1941246Notes

Reaction equation

HRID 1941246 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1)[CH2:3][CH2:4][OH:5].[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.CCOC(C)=O>C(Cl)Cl>[CH:15]1([O:14][C:8]2[CH:7]=[C:6]([CH:2]([N:1]3[C:23](=[O:24])[C:22]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]4[C:20]3=[O:25])[CH2:3][CH2:4][OH:5])[CH:11]=[CH:10][C:9]=2[O:12][CH3:13])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8857Ethyl AcetateHCID 214605133-Amino-3-(3'-cyclopentyloxy-4'methoxyphenyl)-1-propanol

Product 1

HCID 214605383-(3'-Cyclopentyloxy-4'-methoxyphenyl)-3-phthalimido-1-propanolYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-amino-3-(3'-cyclopentyloxy-4'methoxyphenyl)-1-propanol (4.31 grams, 16.24 mmol) and phthalic anhydride (2.41 grams, 16.27 mmol) was melted with a heat gun for 6 minutes. The mixture was allowed to cool to room temperature. Chromatography (silica gel 100 grams, 1:5 EtOAc:CH2Cl2) gave 3-(3'-cyclopentyloxy-4'-methoxyphenyl)-3-phthalimido-1-propanol as solid, (4.97 grams, 77% yield): mp, 59.0°-61.0° C.; 1H NMR (CDCl3)δ1.56-1.98 (m, 9H, OH, C5H8), 2.48-2.59 (m, 1H, CHH), 2.71-2.83 (m, 1H, CHH), 3.66-3.74 (m, 2H, OCH2), 3.80 (s, 3H, CH3), 4.74-4.80 (m, 1H, CH), 5.51 (dd, J=6.5, 9.4 Hz, 1H, NCH), 6.78 (J=8.3 Hz, 1H, Ar), 7.05-7.09 (m, 1H, Ar), 7.16-7.17 (m, 1H, Ar), 7.64-7.70 (m, 2H, Ar), 7.75-7.81 (m, 2H, Ar); 13C NMR (CDCl3)δ24.02, 32.71, 38.84, 51.44, 55.94, 59.75, 80.35, 111.58, 115.06, 120.54, 123.12, 131.60, 131.80, 133.86, 147.48, 149.55, 168.43; Anal Calcd for C23H25NO5 : C, 69.86; H, 6.37; N, 3.54. Found: C, 69.51; H, 6.41; N, 3.54.

Sources & evidence

ORD record
ord-e0fb5ffe1160453b8116532513ef5db4
Source dataset
uspto-grants-1997_12
Patent number
US05703098

Reaction notes

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