Benzylamine → 2,3-Dihydro-5-methoxy-6-(phenylmethoxy)-2-(phenylmethyl)-1H-isoindole

HRID 863907Notes

Reaction equation

HRID 863907 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:4]=1[CH2:19]Cl.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:10][O:9][C:7]1[CH:8]=[C:3]2[C:4](=[CH:5][C:6]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:19][N:28]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:2]2

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 10591097Bis(chloromethyl)-4-methoxy-5-(phenylmethoxy)benzene

Product 1

HCID 107363032,3-Dihydro-5-methoxy-6-(phenylmethoxy)-2-(phenylmethyl)-1H-isoindole

Procedure

The procedure of Example 26 is repeated using 1.0 g of bis(chloromethyl)-4-methoxy-5-(phenylmethoxy)benzene and 0.6 mL of benzyl amine. This affords 0.74 g of the desired product as a beige solid. mp 94°-96° C. MS(FAB): m/z 346 (M+H). Calcd for C23H23NO2 0.05M CH2Cl2 : C=79.16, H=6.66, N=4.01 Found C=78.96, H=6.76, N=3.87

Sources & evidence

ORD record
ord-52618f2b9f4a4611bab29f346a274cad
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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