2-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine → 2-(7-propyl-3,7-dihydro-2H-[1,4]dioxino[2,3-e]indol-9-yl)ethanamine

HRID 1404157Notes

Reaction equation

HRID 1404157 reaction equation
C(OC1C(F)=CC=C2C=1C(CCN(C)C)=CN2)C1C=CC=CC=1.[CH2:24]([N:27]1[C:35]2[C:30](=[C:31]3[O:39][CH2:38][CH2:37][O:36][C:32]3=[CH:33][CH:34]=2)[C:29]([CH2:40][C:41]([NH2:43])=O)=[CH:28]1)[CH2:25][CH3:26]>>[CH2:24]([N:27]1[C:35]2[C:30](=[C:31]3[O:39][CH2:38][CH2:37][O:36][C:32]3=[CH:33][CH:34]=2)[C:29]([CH2:40][CH2:41][NH2:43])=[CH:28]1)[CH2:25][CH3:26]

Participants

3

Reactant 2

HCID 669270882-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamineHCID 669272262-(7-propyl-3,7-dihydro-2H-[1,4]dioxino[2,3-e]indol-9-yl)acetamide

Product 1

HCID 509954502-(7-propyl-3,7-dihydro-2H-[1,4]dioxino[2,3-e]indol-9-yl)ethanamineYield 9%

Procedure

Following the procedure (step 6, scheme 1) used to prepare compound 1-7a, compound 40-6 gave compound 40-7 (5 mg, 9%) as yellow oil. 1H NMR (300 MHz, MeOD-d6): δ (ppm) 6.87 (s, 1H), 6.73 (d, J=8.8 Hz, 1H), 6.61 (d, J=8.8 Hz, 1H), 4.26-4.24 (m, 2H), 4.16-1.15 (m, 2H), 3.91 (t, J=7.2 Hz, 2H), 3.13 (t, J=7.2 Hz, 2H), 3.02 (t, J=7.2 Hz, 2H), 1.71 (q, J=7.2 Hz, 2H), 0.80 (t, J=7.2 Hz, 3H). LCMS: calc 260.2 found 261.1 [MH]+.

Sources & evidence

ORD record
ord-1545820b104a4d91b412078b96f5ac1a
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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