1-Iodopropane → HCID 22396722, compound

HRID 1356348Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12]2[C:13]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20][C:14]=3[NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)[CH2:2][CH3:3].I[CH2:26][CH2:27][CH3:28]>>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12]2[C:13]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20][C:14]=3[NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH2:26][CH2:27][CH3:28]

Participants

Reactant 2

HCID 336431-Iodopropane

HCID 22396800HCID 22396800, compound

Product 1

HCID 22396722HCID 22396722, compound

Procedure

Following the procedure for the preparation of 10-(2-propoxyphenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole and substituting 1-iodohexane for 1-iodopropane while making non-critical variations the title compound was obtained as 360 mg (66%) of a yellow foam: 1H NMR (400 MHz, CDCl3) δ 7.83 (br s, 1H), 7.36-7.27 (m, 3 H), 7.17-7.13 (m, 1H), 7.05-7.01 (m, 1H), 6.98 (d, J=8.2 Hz, 1H), 6.93 (d, J=7.2 Hz, 1H), 3.95-3.85 (m, 2H), 3.12-3.10 (m, 1H), 3.06-3.01 (m, 1H), 2.98-2.93 (m, 2H), 2.90-2.85 (m, 1H), 2.82-2.79 (m, 1H), 2.42-2.37 (m, 2H), 1.57-1.51 (m, 2H), 1.22-1.16 (m, 6 H), 0.83 (t, J=6.9 Hz, 3 H); HRMS (FAB) calcd for C24H30N2O+H1: 363.2436 found 363.2444.

Sources & evidence

ORD record: ord-aa409f5d56c3470b957bc060113612f7
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586421B2

Reaction notes

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