Potassium Bromide → 8-[1,4]Diazepan-1-yl-quinoline

HRID 1250155Notes

Reaction equation

C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:10][CH2:9]1)=O)(C)(C)C.[K+].[Br-]>>[N:11]1([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 701175154-Quinolin-8-yl-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 183273058-[1,4]Diazepan-1-yl-quinolineYield 100%

Procedure

The title compound was prepared according to the procedure of Example 1, Step 6 except that 4-quinolin-8-yl-[1,4]diazepane-1-carboxylic acid tert-butyl ester was used in place of 4-(2-methoxy-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester. Yield: 100%; 1H NMR (300 MHz, CDCl3): δ2.05 (pent, J=6.2 Hz, 2H), 3.11 (t, J=5.7, Hz, 2H), 3.31 (t, J=5.6 Hz, 2H), 3.68 (t, J=6.0 Hz, 2H), 3.75 (t, J=6.0 Hz, 2H), 4.47 (brs, 1H), 7.09 (dd, J=1.4, 7.4 Hz, 1H), 7.28-7.39 (m, 3H), 8.02 (dd, J=1.5, 7,5 Hz, 1H), 8.78 (d, J=1.4 Hz, 1H); IR (KBr, cm−1): 3309w; MS (ES) m/z (relative intensity): 228 (M++H, 60).

Sources & evidence

ORD record: ord-20b0a836e5a642a3953293241b8fc8c6
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337326B1

Reaction notes

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