Nitrogen mustard hydrochloride → 4-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidine-4-carbonitrile

HRID 1397277Notes

Reaction equation

HRID 1397277 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][C:14]#[N:15])[N:12]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:18][CH2:19][N:20]([CH2:22][CH2:23]Cl)[CH3:21]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3([C:14]#[N:15])[CH2:23][CH2:22][N:20]([CH3:21])[CH2:19][CH2:18]3)[N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 5935Nitrogen mustard hydrochlorideHCID 51527842-[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]acetonitrile

Product 1

HCID 673228324-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidine-4-carbonitrileYield 32%

Procedure

This compound was synthesized from 2-(2-(4-chlorophenyl)thiazol-4-yl)acetonitrile and 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride as described in example 16 step 1b (350 mg, yield 32%). 1H NMR (300 MHz, CDCl3) δ 7.91-7.88 (d, J=8.6 Hz, 2H), 7.43-7.40 (d, J=8.6 Hz, 2H), 7.32 (s, 1H), 3.03-2.98 (m, 2H), 2.57-2.38 (m, 7H), 2.26-2.21 (m, 2H). MS (ESI) m/z: Calculated for C16H16ClN3S: 317.08. found: 318.2 (M+H)+.

Sources & evidence

ORD record
ord-6d42fc16dcdc4f4e9207fd6d2b82a921
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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