(R)-5-dibenzylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole → (R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

HRID 1419169Notes

Reaction equation

C([N:8](CC1C=CC=CC=1)[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24])C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of (R)-5-dibenzylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole (1.08 g, 2.64 mmol) and 20% palladium hydroxide on carbon (0.6 g) in absolute ethanol (25 mL) was shaken under a hydrogen atmosphere (3 atm) at 40 °C. for 4 hours. The resulting mixture was filtered through diatomaceous earth, and the filtrate was evaporated under reduced pressure to afford the title compound (0.60 g, 2.62 mmol, 99%) as a white foam: 1H NMR (DMSO-d6) δ 10.65 (br s, NH), 7.14 (d, J=2.2 Hz, 1H), 7.12 (d, J=8.6 Hz, 1H), 6.85 (d, J=1.6 Hz, 1H), 6.60 (dd, J=2.0 and 8.6 Hz, 1H), 3.63-2.83 (m, 7H), 2.78 (s, 3H), 2.05-1.67 (m, 4H); [α]25 =+9° (MeOH, c=1.0); HRMS calculated for C14H19N3: 229.1575; found: 229.1593.

Workup

filtrationThe resulting mixture was filtered through diatomaceous earth
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-2a40d0e6a7c64b9c9c47c39246f87aef
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05886008

Reaction notes

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