2-(4-Chlorophenyl)ethylamine → N-[2-(4-chlorophenyl)ethyl]-2-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3-indol]-1'(2'H)-yl)methyl]benzamide

HRID 1965732Notes

Reaction equation

HRID 1965732 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C1(CN)CCCCC1.[O:19]=[C:20]1[C:28]2([CH2:32][O:31][C:30]3[CH:33]=[C:34]4[C:38](=[CH:39][C:29]2=3)[CH2:37][CH2:36][O:35]4)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]1[CH2:40][C:41]1[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=1[C:43](O)=[O:44].O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC1C=C(C=CC=1)C(O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:43](=[O:44])[C:42]2[CH:46]=[CH:47][CH:48]=[CH:49][C:41]=2[CH2:40][N:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]3([CH2:32][O:31][C:30]4[CH:33]=[C:34]5[C:38](=[CH:39][C:29]3=4)[CH2:37][CH2:36][O:35]5)[C:20]2=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 674302-(4-Chlorophenyl)ethylamineHCID 76688CyclohexanemethylamineHCID 593522533-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]benzoic acidHCID 593523082-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]benzoic acid

Product 1

HCID 59352756N-[2-(4-chlorophenyl)ethyl]-2-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3-indol]-1'(2'H)-yl)methyl]benzamide

Procedure

Following the procedure as described in EXAMPLE 12 and making non-critical variations using 2-(4-chlorophenyl)ethylamine to replace cyclohexanemethylamine, and 2-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzoic acid to replace 3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3-indol]-1′(2′H)-yl)methyl]benzoic acid, N-[2-(4-chlorophenyl)ethyl]-2-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3-indol]-1′(2′H)-yl)methyl]benzamide was obtained (78%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.59 (br, 1H), 7.44-7.23 (m, 7H), 7.23-6.11 (m, 2H), 7.10-6.94 (m, 2H), 6.73 (d, J=7.7 Hz, 1H), 6.52 (s, 1H), 6.40 (s, 1H), 4.94-4.65 (m, 4H), 4.47 (t, J=8.6 Hz, 2H), 3.57-3.42 (m, 2H), 2.95 (t, J=8.3 Hz, 2H), 2.84 (t, J=6.7 Hz, 2H); MS (ES+) m/z 573.1 (M+23).

Sources & evidence

ORD record
ord-e451577039eb4ea08b9258fb10ca0317
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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