Propanal → HCID 18353217, compound

HRID 429827Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH3:11])=[CH:5][CH:4]=1.[CH:27](=O)[CH2:28][CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([N:12]([CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:18][CH2:19]2)[CH2:27][CH2:28][CH3:29])[CH3:11])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 22 °C

Procedure

A mixture of N-[2-(4-methoxyphenyl)-1-methylethyl]-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine (0.87 grams, 2.4 mmole), propionaldehyde (0.2 ml, 2.5 mmole) and sodium triacetoxyborohydride (0.763 grams, 3.6 mmole) in 1,2-dichloroethane (25 ml) was stirred at 22° C. for 16 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between 100 ml ethyl ether and 25 ml 10% aqueous sodium carbonate. The dried (anhydrous magnesium sulfate) and concentrated organic phase was subjected to flash chromatography over silica gel 230-400 mesh eluting with 10% ethyl acetate/hexane. Product fractions were concentrated under reduced pressure to give N-[2-(4-methoxyphenyl)-1-methylethyl]-N-propyl-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)amine as a syrup (0.93 grams, 95%), M+H 405.

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was partitioned between 100 ml ethyl ether and 25 ml 10% aqueous sodium carbonate
dry with materialThe dried (anhydrous magnesium sulfate) and concentrated organic phase
washeluting with 10% ethyl acetate/hexane
concentrationProduct fractions were concentrated under reduced pressure

Sources & evidence

ORD record: ord-82d72585c1cf40f393a0b525c227e5f3
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06319920B1

Reaction notes

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