Ethyl 4-(2-aminoethyl)-1-benzyl-3-hydroxypiperidine-4-carboxylate → 8-Benzyl-6-hydroxy-2,8-diazaspiro[4.5]decan-1-one

HRID 1848527Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][C:4]1([C:18]([O:20]CC)=O)[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH:5]1[OH:17]>CO.N>[CH2:10]([N:7]1[CH2:8][CH2:9][C:4]2([C:18](=[O:20])[NH:1][CH2:2][CH2:3]2)[CH:5]([OH:17])[CH2:6]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Into a 10000-mL 3-necked round-bottom flask was placed a solution of ethyl 4-(2-aminoethyl)-1-benzyl-3-hydroxypiperidine-4-carboxylate (220 g, 718.02 mmol, 1.00 equiv) in methanol (2000 mL) and ammonia (2000 mL). The resulting solution was stirred overnight at 45° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol to obtain the title compound.

Workup

customInto a 10000-mL 3-necked round-bottom flask was placed
concentrationThe resulting mixture was concentrated under vacuum
washeluted with dichloromethane/methanol

Sources & evidence

ORD record: ord-f737ead00d6a4ba0bd6fc572a2d3c7c2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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