1-Iodopropane → HCID 22396966, compound

HRID 2307029Notes

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

Participants

Reactant 2

HCID 336431-Iodopropane

HCID 22396800HCID 22396800, compound

Product 1

HCID 22396966HCID 22396966, 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 (bromomethyl)cyclopropane for 1-iodopropane while making non-critical variations the title compound was obtained as 74 mg (14%) of a brown oil: 1H NMR (400 MHz, CDCl3) δ 7.92 (br s, 1 H), 7.29-7.21 (m, 2 H), 7.12 (d, J=8.0 Hz, 1 H), 7.07-7.03 (m, 1 H), 6.98-6.94 (m, 1 H), 6.92 (d, J=8.2 Hz, 1 H), 6.86 (d, J=7.1 Hz, 1 H), 3.70 (d, J=6.3 Hz, 2 H), 3.01-2.95 (m, 2 H), 2.85-2.73 (m, 4 H), 2.37-2.31 (m, 2 H), 0.95-0.93 (m, 1 H), 0.30-0.25 (m, 2 H), 0.00-(−0.03) (m, 2 H); HRMS (FAB) calcd for C22H24N2O+H1: 333.1967 found 333.1955.

Sources & evidence

ORD record: ord-50da15c501bb4daf920ae1bca6b664f3
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828314B2

Reaction notes

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