Thionyl Chloride → N1-((1H-indol-7-yl)methyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine

HRID 628674Notes

Reaction equation

HRID 628674 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][N:11]([CH:24]2[C:33]3[N:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH2:27][CH2:26][CH2:25]2)[CH2:12][CH2:13][CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)[CH:3]=[CH:2]1.S(Cl)(Cl)=O>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][N:11]([CH:24]2[C:33]3[N:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH2:27][CH2:26][CH2:25]2)[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59176539HCID 59176539, compound

Product 1

HCID 59176547N1-((1H-indol-7-yl)methyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamineYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(((1H-indol-7-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)butylcarbamate, 6, (0.27 g, 0.60 mmol) in methanol (5 mL) was treated with thionyl chloride (1 mL) at room temperature. The resulting mixture was stirred for 30 min. The reaction mixture was then concentrated and dried under reduced pressure to afford 0.26 g (87% yield) of the desired product, B: 1H NMR (400 MHz, d6-DMSO) δ 11.97 (bs, 1H), 8.44 (d, J=4.8 Hz, 1H), 7.59 (d, J=7.2 Hz, 1H), 7.53 (d, J=7.2 Hz, 1H), 7.48-7.40 (m, 1H), 7.35-7.20 (m, 2H), 6.98 (t, J=6.8 Hz, 1H), 6.44 (bs, 1H), 4.90-4.78 (m, 2H), 3.60-3.53 (m, 2H), 3.10-3.00 (m, 2H), 2.80-2.60 (m, 4H), 2.50-2.39 (m, 1H), 2.30-1.40 (m, 7H); ESI+ MS: m/z (rel intensity) 349.2 (100, [M+H]+).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-7d636110afa941f084f341e3b0c63f75
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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