Sodium hydride → HCID 59349565, compound

HRID 415073

Reaction equation

HRID 415073 reaction equation
[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5](OCCCN2CCN(C(OC(C)(C)C)=O)CC2)=[C:4](C)[CH:3]=1.[C:27]([N:34]1[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36][CH2:35]1)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[H-].[Na+].[Cl:43][C:44]1[CH:49]=[C:48](F)[CH:47]=[CH:46][C:45]=1[N+:51]([O-:53])=[O:52]>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:40][CH:37]2[CH2:38][CH2:39][N:34]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:35][CH2:36]2)=[CH:23][C:24]=1[Cl:25].[Cl:43][C:44]1[CH:49]=[C:48]([CH:47]=[CH:46][C:45]=1[N+:51]([O-:53])=[O:52])[O:40][CH:37]1[CH2:38][CH2:39][N:34]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:35][CH2:36]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 750172-Chloro-4-fluoro-1-nitrobenzeneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 59349545Tert-butyl 4-(3-(4-amino-5-chloro-2-methylphenoxy)propyl)piperazine-1-carboxylate

Product 2

HCID 59349565HCID 59349565, compoundHCID 593495781,1-Dimethylethyl 4-(4-amino-3-chlorophenoxy)-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(4-amino-3-chlorophenoxy)piperidine-1-carboxylate was prepared in the same manner as tert-Butyl 4-(3-(4-amino-5-chloro-2 methylphenoxy)propyl)piperazine-1-carboxylate. Reaction of N-Boc-4-hydroxypiperidine with sodium hydride in anhydrous THF, followed by 2-chloro-4-fluoro-1-nitrobenzene (commercially available from Acros) gave tert-butyl 4-(3-chloro-4-nitrophenoxy)piperidine-1-carboxylate. Reduction of the tent-butyl 4-(3-chloro-4-nitrophenoxy)piperidine-1-carboxylate using ammonium formate and iron dust in refluxing toluene-water mixture gave tert-butyl 4-(4-amino-3-chlorophenoxy)piperidine-1-carboxylate in 79% yield. 1H-NMR (400 MHz, CDCl3): δ 6.88 (m, 1H), 6.70 (m, 2H), 4.26 (m, 1H), 3.79 (s, br, 2H), 3.68 (m, 2H), 3.30 (m, 2H), 1.86 (m, 2H), 1.71 (m, 2H), 1.56 (s, 9H). MS (EI): 227 (MH+).

Sources & evidence

ORD record
ord-3f339d4a163a426ca945d64b95ab6383
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Linked notes

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