Propionyl chloride → HCID 131724538, compound

HRID 1836580Notes

Reaction equation

[C:1]([Cl:5])(=O)[CH2:2][CH3:3].[ClH:6].Cl.[CH:8]1[CH:17]=[CH:16][C:15]2[CH2:18][CH2:19][CH2:20][N:13]3[C:14]=2[C:9]=1[C@H:10]1[CH2:23][NH:22][CH2:21][C@H:11]1[CH2:12]3>>[ClH:5].[ClH:6].[CH2:1]([N:22]1[CH2:23][C@H:10]2[C@H:11]([CH2:12][N:13]3[CH2:20][CH2:19][CH2:18][C:15]4[CH:16]=[CH:17][CH:8]=[C:9]2[C:14]3=4)[CH2:21]1)[CH2:2][CH3:3]

Participants

Reactant 2

HCID 62324Propionyl chloride

HCID 131724533HCID 131724533, compound

Product 1

HCID 131724538HCID 131724538, compound

Procedure

Using propionyl chloride and following the procedures described in EXAMPLE 102, (±)-cis-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline free base from EXAMPLE 11 was converted into the title compound of EXAMPLE 103 as an off-white powder. 1H NMR (dmso-D6) δ: 11.10 (broad s, 1H), 6.90-6.77 (m, 2H), 6.63-6.55 (m, 1H), 3.99-3.90 (m, 1H), 3.85-3.75 (m, 1H), 3.67-3.58 (m, 1H), 3.50-3.35 (m, 2H), 3.15-2.93 (m, 4H), 2.90-2.75 (m, 3H), 2.70-2.63 (m, 2H), 1.95-1.85 (m, 2H), 1.70-1.59 (m, 2H), 0.91-0.82 (m, 3H). LRMS (ES)+: 257.1 (M+H)+.

Sources & evidence

ORD record: ord-767ed7da124c42dca359e5092673d7ad
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777406B2

Reaction notes

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