Potassium Carbonate → Tert-butyl-2-((2-tert-butoxybenzyl)(6-(4-(2-methoxyphenyl)piperidin-1-yl)hexyl)amino)ethylcarbamate

HRID 403123Notes

Reaction equation

HRID 403123 reaction equation
[C:1]([O:5][C:6]1[CH:41]=[CH:40][CH:39]=[CH:38][C:7]=1[CH2:8][N:9]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:4])([CH3:3])[CH3:2].BrCCCCCCN(CC1C=CC=CC=1OC(C)(C)C)CCN[C:53](=O)[O:54]C(C)(C)C.COC1CC(C2C=CC=CC=2)CCN1.C([O-])([O-])=O.[K+].[K+]>>[C:15]([O:14][C:13](=[O:19])[NH:12][CH2:11][CH2:10][N:9]([CH2:8][C:7]1[CH:38]=[CH:39][CH:40]=[CH:41][C:6]=1[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=2[O:54][CH3:53])[CH2:28][CH2:27]1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 671282442-Methoxy-4-phenylpiperidineHCID 70896342Tert-butyl 2-((2-tert-butoxybenzyl)(6-(4-phenylpiperidin-1-yl)hexyl)amino)ethylcarbamateHCID 86672687Tert-butyl 2-((6-bromohexyl)(2-tert-butoxybenzyl)amino)ethylcarbamate

Product 1

HCID 131731436Tert-butyl-2-((2-tert-butoxybenzyl)(6-(4-(2-methoxyphenyl)piperidin-1-yl)hexyl)amino)ethylcarbamateYield 63.4%

Procedure

The same procedure as described for compound 16 was applied to starting material 15 (1.9 g, 4.66 mmol), 2-methoxy-4-phenylpiperidin (1.338 g, 6.99 mmol) and K2CO3 (0.644 g, 4.66 mmol). Purification was carried out on a silica gel TLC plate that was developed in with a 3% methanolic NH3 (7 M NH3 in methanol/97% CH2Cl2. The product was isolated as pale yellow oil (63.4%). Mass Spec.=596.44 (M+H)+.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-32d43d4e5a634f8091ce0d5af64aefad
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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