Trifluoroacetic acid → 2-[3-[(3-Aminopropyl)methylamino]propyl]-3a,9b-dihydro-benzo[de]isoquinoline-1,3-dione

HRID 12259Notes

Reaction equation

HRID 12259 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:13][CH2:14][CH2:15][N:16]1[C:25](=[O:26])[CH:24]2[CH:27]=[CH:28][CH:29]=[C:22]3[CH:23]2[C:18](=[CH:19][CH:20]=[CH:21]3)[C:17]1=[O:30])[CH3:12])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[CH2:13][CH2:14][CH2:15][N:16]1[C:25](=[O:26])[CH:24]2[CH:27]=[CH:28][CH:29]=[C:22]3[CH:23]2[C:18](=[CH:19][CH:20]=[CH:21]3)[C:17]1=[O:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86612376[3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester

Product 1

HCID 866123752-[3-[(3-Aminopropyl)methylamino]propyl]-3a,9b-dihydro-benzo[de]isoquinoline-1,3-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester (0.34 g, 0.81 mmol) in CH2Cl2 (24 ml) was added trifluoroacetic acid (6 ml). The reaction mixture was stirred at room temperature for 16 h at which point the reaction was completed by TLC. All solvents were removed under reduced pressure to give 2-[3-[(3-aminopropyl)methylamino]propyl]-3a,9b-dihydro-benzo[de]isoquinoline-1,3-dione (0.24 g, 92%) as an oil, which was used directly in the next reaction. 1H-NMR [MeOD, _, ppm]: 8.64 (m, 2H), 8.54 (m, 2H), 7.92 (m, 2H), 4.45 (m, 2H, 2CH2NO), 3.55 (m, 4H, 2CH2), 3.33 (m, 2H, CH2), 3.22 (s, 3H, N(CH3)), 2.44 (m, 4H, 2(CH2)).

Workup

  1. customAll solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-146cb0dd04144bee85c6a1e7e2520d6e
Source dataset
uspto-grants-2010_06
Patent number
US07728000B2

Reaction notes

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