Trifluoroacetic acid → (RS) 2-(4-chlorophenoxymethyl)-4-[5-(piperidin-3-yl)pentoxy]-1-[3-(piperidin-3-yl)propyl]-benzimidazole

HRID 1384000Notes

Reaction equation

[Cl:1][C:2]1[CH:53]=[CH:52][C:5]([O:6][CH2:7][C:8]2[N:12]([CH2:13][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]3)[C:11]3[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]4[CH2:44][CH2:43][CH2:42][N:41](C(OC(C)(C)C)=O)[CH2:40]4)[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[N:12]([CH2:13][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]3)[C:11]3[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]4[CH2:44][CH2:43][CH2:42][NH:41][CH2:40]4)[C:10]=3[N:9]=2)=[CH:52][CH:53]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 21188592(RS) 2-(4-chlorophenoxymethyl)-4-[5-[1-(t-butoxycarbonyl)piperidin-3-yl]pentoxy]-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole

Product 1

HCID 21188762(RS) 2-(4-chlorophenoxymethyl)-4-[5-(piperidin-3-yl)pentoxy]-1-[3-(piperidin-3-yl)propyl]-benzimidazole

Procedure

The title product is prepared from (RS) 2-(4-chlorophenoxymethyl)-4-[5-[1-(t-butoxycarbonyl)piperidin-3-yl]pentoxy]-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]benzimidazole using a standard trifluoroacetic acid deprotection protocol.

Sources & evidence

ORD record: ord-8220b9732c7745459da9586f1b4a7e94
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255494B1

Reaction notes

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