1-Iodopropane → HCID 22397011, compound

HRID 1370465Notes

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]C>>[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][CH3:27]

Participants

Reactant 2

HCID 336431-Iodopropane

HCID 22396800HCID 22396800, compound

Product 1

HCID 22397011HCID 22397011, 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-iodopentane for 1-iodopropane while making non-critical variations the title compound was obtained as 361 mg (71%) of a brown oil: 1H NMR (400 MHz, CDCl3) δ 7.83 (br s, 1H), 7.36-7.28 (m, 3H), 7.17-7.13 (m, 1H), 7.05-7.01 (m, 1H), 6.97 (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), 3.06-3.04 (m, 1H), 2.98-2.93 (m, 2H), 2.88-2.85 (m, 1H), 2.81-2.79 (m, 1H), 2.42-2.37 (m, 2H), 1.59-1.52 (m, 2H), 1.21-1.13 (m, 4H), 0.79 (t, J=7.0 Hz, 3H); HRMS (FAB) calcd for C23H28N2O+H1: 349.2280 found 349.2280.

Sources & evidence

ORD record: ord-0aea05465395408bb60a78d8bd4d3012
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583135B2

Reaction notes

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