401502-00-9

Basic information

• Product Name: N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine
• Synonyms: N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine
• CAS NO: 401502-00-9
• Molecular Weight: 209.264
• Mol File: 401502-00-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine(401502-00-9)
• EPA Substance Registry System: N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine(401502-00-9)

Safety Data

• Hazardous Substances Data: 401502-00-9(Hazardous Substances Data)

Upstream product

• 107-11-9 1-amino-2-propene 
• 1129-78-8 1-(3-bromopropoxy)-4-fluorobenzene 

Downstream Products

• 1345718-95-7 tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate 
• 1345718-96-8 (R,R,R)-N(1)-[3'-(4''-fluorophenoxy)propyl]-3-hydroxy-4-[N-benzyl-N-(α-methylbenzyl)amino]-piperidin-2-one 
• 1345718-97-9 (R,R,R)-N(1)-[3'-(4''-fluorophenoxy)propyl]-3-methoxy-4-[N-benzyl-N-(α-methylbenzyl)amino]piperidin-2-one 
• 1345718-98-0 (3S,4R,αR)-N(1)-(3'-(4''-fluorophenoxy)propyl)-3-methoxy-4-[N-benzyl-N-(α-methylbenzyl)amino]piperidine 
• 503433-37-2 C₁₅H₂₃FN₂O₂ 
• 81098-60-4 (+)-(3S,4R)-cisapride 
• 1384276-82-7 tert-butyl (Z)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate 
• 1345718-94-6 tert-butyl (E)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate 

Relevant articles and documents

Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride

A concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)-cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy) propyl]-3-methoxy-4-(2″′-methoxy-4″′-amino- 5″′-chlorobenzamido)piperidine} from commercially available starting materials has been developed. The key step of this synthesis employs the diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(α- methylbenzyl)amide to tert-butyl 5-[N-3′-(4″-fluorophenoxy)propyl-N- allylamino]pent-2-enoate and in situ enolate oxidation with (-)- camphorsulfonyloxaziridine to set the (3S,4R)-configuration found within the piperidine ring of the product. This synthesis proceeds in 9 steps from commercially available 1-(4′-fluorophenoxy)-3-bromopropane with an overall yield of 19%.

Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4- aminopiperidin-2-ones: Application to the asymmetric synthesis of (+)-(3S,4R)-cisapride

The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl) amide to δ-(N-allylamino)-α,β-unsaturated esters, followed by N-deallylation and cyclisation of the resultant β,δ-diamino esters, gives the corresponding 4-aminopiperidin-2-ones as single diastereoisomers (>99:1 dr). Subsequent deprotonation with LiHMDS and functionalisation of the resultant lithium enolate gives 3,4-anti-3-substituted-4-aminopiperidin-2-ones in >99:1 dr. Alternatively, in situ oxidation of the intermediate lithium (Z)-β-amino enolates formed upon conjugate addition gives α-hydroxy-β,δ-diamino esters, which after N-deallylation and cyclisation gives the corresponding 3,4-syn-3-hydroxy-4-aminopiperidin-2-ones in >99:1 dr. The utility of this methodology was successfully demonstrated in a concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)- cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy)propyl]-3-methoxy- 4-(2?-methoxy-4?-amino-5?-chlorobenzamido)piperidine} in nine steps from commercially available starting materials with an overall yield of 19%.