Potassium Carbonate → Tert-butyl 2-((3-(4-benzylpiperidin-1-yl)propyl)(2-tert-butoxybenzyl)amino)ethylcarbamate

HRID 403132Notes

Reaction equation

HRID 403132 reaction equation
[C:1]([O:5]C1C=CC=CC=1CN(CC1C=CC=CN=1)CCCN1CCC(C2C=CC=CC=2)CC1)([CH3:4])([CH3:3])[CH3:2].[CH2:36]([CH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[C:49]([O:53][C:54]1[CH:74]=[CH:73][CH:72]=[CH:71][C:55]=1[CH2:56][N:57]([CH2:67][CH2:68][CH2:69]Cl)[CH2:58][CH2:59][NH:60][C:61](=[O:66])C(C)(C)C)([CH3:52])([CH3:51])[CH3:50].C([O-])([O-])=O.[K+].[K+]>>[CH2:36]([CH:43]1[CH2:48][CH2:47][N:46]([CH2:69][CH2:68][CH2:67][N:57]([CH2:56][C:55]2[CH:71]=[CH:72][CH:73]=[CH:74][C:54]=2[O:53][C:49]([CH3:50])([CH3:51])[CH3:52])[CH2:58][CH2:59][NH:60][C:61](=[O:66])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:45][CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 67128436N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamideHCID 70896369N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine

Product 1

HCID 70896359Tert-butyl 2-((3-(4-benzylpiperidin-1-yl)propyl)(2-tert-butoxybenzyl)amino)ethylcarbamateYield 80%

Procedure

The same procedure as described for compound 20 was applied to 4-benzylpiperidine (0.46 g, 2.63 mmol), compound 23 (0.7 g, 1.75 mmol), KI (0.87 g, 5.25 mmol) and K2CO3 (1.21 g, 8.75 mmol). The residue was purified on a silica gel TLC plate that was developed in 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (80% yield). 1H NMR (CDCl3) δ 7.373 (d, 1H, Ar), 7.264 (m, 2H, Ar), 7.176 (t, 1H, Ar), 7.137 (d, 2H, Ar), 7.137 (d, 2H, Ar), 7.108 (d, 1H, Ar), 7.021 (dd, 1H, Ar), 6.985 (t, 1H, Ar), 3.577 (s, 2H, —CH2—), 3.167 (d, 2H, —CH2—), 2.892 (d, 2H, —CH2—), 2.524 (d, 2H, —CH2—), 2.498 (t, 2H, —CH2—), 2.453 (t, 2H, —CH2—), 2.290 (t, 2H, —CH2—), 1.839 (t, 2H, —CH2—), 1.657 (m, 2H, —CH2—), 1.618 (d, 2H, —CH2—), 1.517 (m, 1H, —CH—), 1.426 (s, 9H, —C(CH3)3, 1.376 (s, 9H, —C(CH3)3, 1.329 (overlapped m, 4H). Mass Spec.=538.77 (M+H)+.

Workup

  1. customThe residue was purified on a silica gel TLC plate that

Sources & evidence

ORD record
ord-e6466a842207460b93b3a12d7894ee7c
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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