Triethylamine → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindole

HRID 1790522Notes

Reaction equation

HRID 1790522 reaction equation
F[C:2]1C=CC(CCN2CCC(N3C4C(=CC=C(CN)C=4)C=C3)CC2)=CC=1.[F:27][C:28]1[CH:57]=[CH:56][C:31]([CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH:37]([N:40]3[C:48]4[C:43](=[CH:44][CH:45]=[C:46]([CH2:49][NH:50][C:51](=[O:55])[CH2:52][CH2:53]Br)[CH:47]=4)[CH:42]=[CH:41]3)[CH2:36][CH2:35]2)=[CH:30][CH:29]=1.BrCCC(Cl)=O.C(N(CC)CC)C>C(#N)C>[F:27][C:28]1[CH:57]=[CH:56][C:31]([CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH:37]([N:40]3[C:48]4[C:43](=[CH:44][CH:45]=[C:46]([CH2:49][N:50]5[CH2:2][CH2:53][CH2:52][C:51]5=[O:55])[CH:47]=4)[CH:42]=[CH:41]3)[CH2:36][CH2:35]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84944Propanoyl chloride, 3-bromo-HCID 131725833HCID 131725833, compound

Product 1

HCID 220379311-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindoleYield 156.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1H-NMR(400 MHz,DMSO-d6); δ(ppm) 1.40-1.50(2H,m), 1.60-1.71(4H,m), 2.00-2.08(2H,m), 2.12-2.26(2H,m), 2.37-2.52(2H,m), 2.70-3.10(8H,m), 3.39-3.49(2H,m), 3.52-3.63(2H,m), 4.42(2H,d,J=6.0 Hz), 4.45-4.58(1H,m), 6.43(1H,d,J=3.2 Hz), 6.96(1H,d,J=8.0 Hz), 7.10-7.19(2H,m), 7.26-7.34(2H,m), 7.44(1H,d,J=3.2 Hz), 7.47(1H,s), 7.49(1H,d,J=8.0 Hz), 8.76(1H,t,J=6.0 Hz). m.p.: 113-114° C. Mass: FAB+477(M+H). Example 377: Synthesis of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-bromopropionylamino)methylindole 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (370 mg) obtained in Example 322-3), 3-bromopropionyl chloride (240 mg), triethylamine (140 mg) and acetonitrile (10 ml) were treated as in Example 373 to give the title compound (290 mg) as an oil (yield: 57%). 1H-NMR(400 MHz,CDCl3); δ(ppm) 2.02-2.10(2H,m), 2.14-2.26(2H,m), 2.29-2.40(2H,m), 2.68-2.76(2H,m), 2.80(2H,t,J=6.4 Hz), 2.85-2.92(2H,m), 3.18-3.26(2H,m), 3.70(2H,t,J=6.4 Hz), 4.20-4.30(1H,m), 4.62(2H,d,J=6.0 Hz), 6.15(1H,br-s), 6.50(1H,d,J=3.2 Hz), 6.96-7.04(3H,m), 7.16-7.24(2H,m), 7.25(1H,d,J=3.2 Hz), 7.37(1H,s), 7.58(1H,d,J=8.0 Hz). Example 378: Synthesis of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-N,N-dimethylaminopropionyl)aminomethylindole

Workup

  1. additionwere treated as in Example 373

Sources & evidence

ORD record
ord-3f70d9f9b5254fe589885b6e3d06d864
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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