1,4-Dioxa-8-azaspiro(4.5)decane → HCID 18511653, compound

HRID 1370535Notes

Reaction equation

HRID 1370535 reaction equation
O1C2(CCNCC2)OCC1.CC1C=C(C=CC=1C)OCCCCN1CCC(=O)CC1.[ClH:31].CN.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)/C=C/C(O)=O.[CH3:56][N:57]([CH:68]1[CH2:73][CH2:72][N:71]([CH2:74][CH2:75][CH2:76][CH2:77][O:78][C:79]2[CH:84]=[CH:83][C:82]([CH3:85])=[C:81]([CH3:86])[CH:80]=2)[CH2:70][CH2:69]1)C(=NC1C=CC=CC=1)SC>>[ClH:31].[ClH:31].[CH3:86][C:81]1[CH:80]=[C:79]([CH:84]=[CH:83][C:82]=1[CH3:85])[O:78][CH2:77][CH2:76][CH2:75][CH2:74][N:71]1[CH2:72][CH2:73][CH:68]([NH:57][CH3:56])[CH2:69][CH2:70]1

Participants

6

Reactant 5

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 9807772HCID 9807772, compoundHCID 18511672HCID 18511672, compound

Product 1

HCID 18511653HCID 18511653, compound

Procedure

1,4-Dibromobutane, condensed with 3,4-dimethylphenol according to Ismaïel et al. (J. Med. Chem., 1993, 36, 2519-25), gives 1-[4-bromobutoxy]-3,4-dimethylbenzene with a yield of 86%. The condensation of this compound (according to the same authors) with 1,4-dioxa-8-azaspiro[4.5]decane gives, after deprotection, 1-[4-(3,4-dimethylphenoxy)butyl]-4-piperidone in the form of an orangey oil with a yield of 61%. The reductive amination of this ketone (4.33 g or 15.7 mmol) with methylamine hydrochloride (1.06 g; 15.7 mmol) in the presence of sodium triacetoxyborohydride (4.33 g; 20.5 mmol) according to the protocol of Example 3.1 makes it possible to prepare 5.95 g (Yd: 63%) of the compound of formula 10:

Workup

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Sources & evidence

ORD record
ord-a7ffe46810df4eaf8cdd0680e3d0941c
Source dataset
uspto-grants-2003_06
Patent number
US06583159B1

Reaction notes

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